HoltonWiseTV Highlights (69)

Someone is STILL INSIDE this house, and we're here to carry out an eviction! We're taking you along for another real-life eviction as our crew arrives at a rental property and hears someone making noise inside. What's going to happen when we attempt to take possession of the property? This is the side of real estate investing that nobody likes to talk about! Whether you're investing in Cleveland, Detroit, Chicago, Baltimore, or other rental markets across America, dealing with problem tenants, nonpayment of rent, and evictions is part of the risk of being a landlord. That's why professional tenant screening, effective property management, and a solid investment strategy are so important, especially for out-of-state investors and landlords working with Section 8 rentals. Subscribe to HoltonWiseTV to watch this live eviction footage and see what happens when we show up to take back the property!

Squatters absolutely DESTROYED this foreclosed property, but where most people see a disaster, experienced real estate investors see an opportunity! On HoltonWiseTV we take you inside completely trashed foreclosures that need top-to-bottom renovations. This is what BRRRR investing looks like before the profits! Buying distressed properties, renovating them, renting them out, and refinancing is how investors build wealth in markets like Cleveland, Detroit, and Indianapolis. The ugly properties are often where the biggest opportunities are hiding. If you're an out-of-state investor looking for foreclosure deals, fixer-uppers, Section 8 rentals, or cash-flowing investment properties, the HoltonWise team can help with acquisitions, construction, financing connections, and property management.

Section 8 investing can make you a lot of money, but let's talk about the elephant in the room: government dependency, personal responsibility, and the challenges of managing low-income rental properties. James Wise of HoltonWiseTV explains why he believes needing taxpayer-funded housing assistance is a red flag and why Section 8 landlords need to understand the hassle factor that comes with this investment strategy. Government-backed rental payments can create tremendous cash flow, but they don't eliminate the risks of property damage, difficult tenants, unpaid tenant portions, or expensive evictions. Does relying on government assistance say something about a person's self-sufficiency, or is that an unfair way to judge someone? We're tackling that controversial question head-on. Whether you're investing in Cleveland, Detroit, Chicago, Baltimore, or other Section 8 markets, successful rental property investing requires professional tenant screening, strong property management, and an understanding that financial assistance alone doesn't determine whether someone will be a responsible tenant.

You think evicting a single mom makes a landlord evil? Then why don't YOU pay her rent? Everybody loves calling landlords greedy, heartless parasites when they see a tenant getting evicted, but nobody wants to talk about the thousands of dollars in unpaid rent, property taxes, insurance, mortgages, and maintenance costs the landlord is still responsible for paying. Here at HoltonWise, we deal with real evictions, real tenants, and real financial consequences every single day. Being a landlord doesn't mean you're obligated to provide free housing. If you think landlords are wrong for evicting tenants who refuse to pay, put your money where your mouth is! Contact HoltonWise and help cover somebody's unpaid rent. We'll gladly discuss how you can help tenants facing eviction. It's easy to be generous with somebody else's money. Let's see how generous you are with YOURS!

Why keep dealing with nightmare tenants, unpaid rent, and expensive evictions in places like Flint, Michigan, when you could be investing in brand-new rental properties in Montevallo, Alabama? There is an alternative for real estate investors who are tired of the headaches that come with older, low-income Section 8 properties. With over $42,000 in potential incentives and tax savings available through Rent To Retirement, investors have an opportunity to explore new construction rentals without inheriting someone else's tenant problems, deferred maintenance, or renovation nightmares. Whether you're investing from New York, California, Chicago, or anywhere else in the country, it's time to compare the numbers and decide which investment strategy makes more sense for you. Keep fighting evictions or explore new construction with financial incentives. Your choice!

Cleveland keeps changing the rules on landlords, and if you're investing in Cleveland rental properties, staying on top of lead certification requirements can feel like playing whack-a-mole! Between changing regulations, lawsuits, and shifting compliance procedures, Cleveland real estate investors need somebody who knows exactly what's going on. That's why we partner with PB Free Ohio and lead certification expert Zak Burkons to help our investors navigate the process. Whether you're a local landlord or an out-of-state investor buying Section 8 rental properties in Cleveland, having the right team in place can save you time, money, and headaches. At HoltonWise, we help investors navigate the Cleveland real estate market from acquisition to property management, including coordinating lead compliance with trusted professionals.

When you're investing in rental properties in rough neighborhoods, the biggest risk isn't always the property itself. It's the TENANTS! Nonpaying tenants, property damage, evictions, and nightmare tenants can turn a great real estate deal into a financial disaster. That's why I LOVE buying rental properties that are vacant and rent ready. When you inherit the seller's tenants, you're inheriting their tenant screening decisions, their problems, and potentially their mistakes. But when you buy a vacant property, YOU control the process. You can professionally screen applicants, verify income, review rental history, and establish your own standards while complying with fair housing laws. Whether you're investing in Section 8 rental properties in Cleveland, Detroit, Baltimore, Chicago, or Indianapolis, remember this: A vacant property is often better than a property occupied by a bad tenant. You're buying the real estate, NOT the previous landlord's performance!

When you're investing in low-income neighborhoods, collecting rent is EVERYTHING. That's why I'm such a big believer in Section 8 real estate investing. With traditional tenants, you're relying on their personal finances to cover the rent every month. With Section 8, a substantial portion of that rent can come directly from the government through the Housing Choice Voucher Program. It's not a guarantee against evictions, property damage, or missed payments, but when done right, Section 8 can provide more predictable rental income and stronger cash flow. Whether you're buying rental properties in Cleveland, Detroit, Baltimore, Chicago, or Indianapolis, understanding how to leverage Section 8 can make a massive difference in your investment strategy. Stop gambling on whether your tenants can afford the rent and start learning how government-assisted housing can work for your portfolio.

One of the BIGGEST mistakes real estate investors make when buying Section 8 rental properties is inheriting another landlord's tenants without properly evaluating who they're dealing with! Just because a property is occupied and collecting rent doesn't mean you're buying a good investment. You could be inheriting a nightmare tenant, a future eviction, or years of headaches caused by another landlord's terrible tenant screening practices. At Holton Wise, we've found that the overwhelming majority of our worst tenant problems come from tenants we inherited when acquiring properties from other landlords, NOT tenants we personally screened and placed. That's why we often prefer buying vacant, rent-ready investment properties where we can select our own tenants, conduct thorough background checks, verify rental histories, and properly navigate the Section 8 approval process. Whether you're investing in Cleveland, Detroit, Baltimore, Chicago, or Indianapolis, don't let the promise of immediate rental income blind you to the risks of inheriting someone else's problems. Remember, vacant is better than a bad tenant!

Bad tenants create GREAT seller financing opportunities for real estate investors! Everybody wants the cash flow that comes with owning rental properties, but not everybody can handle the headaches that come with managing difficult tenants. Some landlords get into the business thinking they're going to collect passive income, only to discover the harsh reality of dealing with evictions, property damage, nonpaying tenants, and all the other problems that come with owning rental properties in rough neighborhoods. That's where the opportunity comes in! When landlords get fed up and want OUT, savvy real estate investors can negotiate incredible seller financing deals that allow them to acquire cash-flowing properties with low down payments and favorable terms. Whether you're investing in Cleveland, Detroit, Baltimore, Memphis, or Indianapolis, understanding the hassle factor can help you uncover creative financing opportunities other investors overlook. The seller wants to escape the headaches, and you want to build your rental portfolio. That's how deals get done!

If you're investing in Section 8 rental properties, your property manager needs to understand one very important thing: YOU are the customer, NOT the tenants! Too many Section 8 landlords hire property management companies that forget who they're actually working for. Your property manager's job is to protect your investment, collect rent, enforce leases, handle Section 8 inspections, minimize vacancies, and maximize your cash flow. Think of it like McDonald's. The cattle aren't the customers. They're part of the business operation. That doesn't mean you mistreat them, but it does mean you understand who the business is designed to serve. Whether you're investing in Section 8 housing in Cleveland, Detroit, or Baltimore, you need a property manager who prioritizes your financial interests while treating tenants fairly and following the law. You're not buying rental properties to run a charity. You're investing to make money, and your property manager needs to understand that.

San Francisco real estate investors are competing with billionaires, hedge funds, and international money just to buy overpriced properties that barely cash flow. Meanwhile, savvy investors are building wealth in markets like Cleveland, Detroit, Chicago, and Baltimore by buying the properties everyone else is afraid to touch. Ugly houses, problem tenants, distressed properties, and value-add opportunities are where the real money can be made. While California investors fight over trophy properties, we're looking for Section 8 rentals, BRRRR opportunities, and cash-flowing investment properties with serious upside. Fear creates opportunity. Opportunity creates margins. Margins create wealth. Stop chasing overpriced California real estate and start investing where the numbers actually make sense.

Most real estate sellers think the best way to negotiate is to list their property ABOVE what it's actually worth so buyers have room to talk them down. That's a mistake. In this video, we explain why pricing an investment property correctly from day one can create more buyer demand, attract serious real estate investors, and potentially lead to better offers. Whether you're selling a $45,000 fixer-upper to BRRRR investors or a turnkey rental property to out-of-state investors from New York, California, Chicago, Seattle, or San Francisco, understanding how to price real estate is critical. If you're buying or selling rental properties in markets like Cleveland, Detroit, or Indianapolis, this is a lesson you don't want to miss.

What's one of the weirdest signs of a GREAT Section 8 tenant in New Jersey? A house full of STUFF! That's right—knick-knacks, furniture, decorations, shelves full of personal belongings, and all the little things that make a rental property feel like home. When we're analyzing New Jersey Section 8 rental properties, we LOVE seeing tenants who appear settled in for the long haul. Why? Because tenant turnover is EXPENSIVE! Every vacancy can mean lost rental income, cleaning, repairs, renovations, and the hassle of finding another qualified Section 8 tenant. A tenant who's made a house their home may be more inclined to renew their lease rather than pack everything into a moving truck and start over. Of course, belongings alone don't guarantee a great tenant, but signs of stability are worth paying attention to. Whether you're investing in Newark, Trenton, Camden, Paterson, or other New Jersey Section 8 markets, long-term tenant retention can be a major factor in maximizing rental property cash flow. The best Section 8 investment isn't always about getting a new tenant paying more rent. Sometimes it's about keeping the good tenant you've already got!

Want bigger Section 8 checks in Philadelphia? Stop obsessing over granite countertops, fancy kitchens, and expensive renovations. If you're investing in Philly Section 8 rental properties, bedroom count can be one of the biggest factors influencing your rental income potential! A clean, functional, durable 3-bedroom rental could be a much better investment than a beautifully renovated 2-bedroom property. Philadelphia Section 8 investors need to understand how bedroom count, voucher payment standards, and rent reasonableness impact their potential returns. The goal isn't to build the Taj Mahal for your tenants. It's to provide quality, affordable housing while maximizing cash flow and minimizing unnecessary renovation expenses. Whether you're buying your first Philadelphia rental property or growing an existing Philly Section 8 portfolio, understanding what actually drives rental income can make all the difference. Buy for the numbers, not the fancy finishes!

Nobody wakes up excited to file an eviction. Well, except maybe James Wise! Evictions are expensive, time-consuming, and frustrating, but when tenants stop paying rent, ignore notices, and refuse to follow the lease, eventually landlords have to take action. The reality is simple: landlords aren't running charities, and rental properties aren't free housing. Whether you're investing in Section 8 rentals in Cleveland, Detroit, or Baltimore, dealing with nonpaying tenants is one of the biggest challenges real estate investors face. Out-of-state investors from New York, California, Chicago, Seattle, and other expensive markets need to understand that successful rental property investing means enforcing leases, screening tenants properly, and knowing when it's time to move forward with an eviction. At HoltonWise, we believe in giving tenants a fair opportunity to follow the rules, but when they don't, we're not afraid to enforce the lease through the legal process. You can't stop paying rent and expect to live somewhere forever!

If you're making $300,000 a year, why are you wasting your time chasing broke tenants through eviction court? Successful real estate investors need their money working FOR them, not creating more problems to solve. Between rising taxes, expensive evictions, property damage, and endless tenant headaches, buying another cheap rental might not be your smartest move. Whether you're investing in Cleveland, Detroit, Baltimore, or looking to expand beyond traditional Section 8 rentals, it's time to think bigger. Rent To Retirement offers investment opportunities where qualified investors could potentially benefit from up to $60,000 in combined incentives and tax savings, depending on the property and their individual tax situation. Stop letting taxes and bad tenants eat away at your wealth. Start making your money solve problems instead of creating them!

Why buy Section 8 rentals in neighborhoods that aren't going anywhere when you can buy in areas with massive upside potential? At HoltonWise, we're looking for rental properties that produce strong cash flow TODAY while putting investors in position to benefit from potential appreciation and gentrification TOMORROW. We're talking about Cleveland, Ohio neighborhoods bordering trendy, revitalized areas where major institutions are investing billions of dollars. A duplex collecting $1,350 per unit today could potentially command $2,500 per unit in the future if the surrounding neighborhood continues improving. That's the kind of opportunity we love showing out-of-state investors from expensive markets like Los Angeles, California, and New York City, New York. Section 8 cash flow today, potential market-rate appreciation tomorrow. That's how we approach long-term real estate investing in Cleveland, Detroit, Michigan, and other affordable Midwest markets.

The government might pay the rent, but who's paying to clean up the disaster when a Section 8 tenant moves out? Mouse droppings under the refrigerator, busted cabinets, damaged doors, and a whole lot of work waiting for our property management crew. Welcome to the side of Section 8 real estate investing nobody puts in the sales pitch. Whether you're buying rental properties in Cleveland, Ohio, Detroit, Michigan, or Memphis, Tennessee, collecting rent is only half the battle. Bad tenants, expensive turnovers, and unexpected repairs can eat your cash flow alive. At HoltonWise, we're showing investors what actually happens behind the scenes because making money in real estate isn't just about collecting rent checks. It's about managing the headaches that come with them.

One eviction 25 years ago and you're STILL denied? That's how strict some landlords are when it comes to tenant screening. At HoltonWise, we're in the business of making money with rental properties, not gambling our investors' cash flow on risky tenants. Whether you're investing in Section 8 rentals in Cleveland, Ohio, Detroit, Michigan, or Memphis, Tennessee, tenant screening is one of the most important parts of protecting your investment. One bad tenant can cost thousands in unpaid rent, property damage, legal fees, and eviction expenses. James Wise explains why he believes past evictions are a major red flag and why landlords need to prioritize protecting their rental portfolios over giving second chances.

Tired of dealing with endless evictions, problem tenants, and aging rental properties in Baltimore, Maryland? There's another way to invest in real estate. Through Rent To Retirement, investors can purchase brand-new rental properties in Katy, Texas, with over $41,000 in potential incentives and tax savings. Instead of constantly battling tenants, paying for repairs, and dealing with expensive turnovers, you could be building a rental portfolio with new construction in one of the fastest-growing areas of Texas. Whether you're investing in Baltimore, Cleveland, Detroit, or looking to expand into landlord-friendly markets like Katy, Texas, the goal is the same: maximize your returns while minimizing your headaches. The choice is yours!

Bad tenants hate their landlords. Good tenants get along with their landlords just fine! In the news we hear plenty of horror stories about terrible landlords and nightmare tenants, but here's the side of Cleveland real estate investing that doesn't get nearly enough attention. When tenants pay their rent, respect the property, and communicate with management, and landlords hold up their end of the bargain, everybody wins. This Cleveland, Ohio tenant loves our property management team so much that she's moving out of one of our rentals and into ANOTHER! That's what happens when good tenants and professional property managers work together. For out-of-state investors from New York, Los Angeles, and beyond, having a reliable team managing your Cleveland Section 8 and traditional rental properties is essential to building a successful real estate portfolio.

Most real estate investors see a trashed house and run the other way. We see opportunity. The uglier the property, the fewer buyers we're competing against, and less competition can mean bigger discounts, better spreads, and more potential profit. At HoltonWise, we specialize in finding these overlooked investment opportunities and turning distressed properties into cash-flowing rental assets. Whether you're looking to BRRRR, flip, or build a Section 8 rental portfolio, markets like Cleveland, Ohio, Detroit, Michigan, and Indianapolis, Indiana offer opportunities for out-of-state investors from New York, Los Angeles, and other expensive real estate markets. The money isn't always in buying the prettiest house. Sometimes the biggest paydays come from buying the properties nobody else wants.

New York landlords, grab some popcorn. While landlords in tenant-friendly markets like New York City struggle with lengthy and expensive eviction proceedings, investors in more landlord-friendly markets have a different experience when tenants stop paying rent. On HoltonWiseTV, we show you what the eviction process looks like outside of New York and why out-of-state real estate investors from NYC, Los Angeles, and other expensive markets are exploring Section 8 rental properties in Cleveland, Ohio, Detroit, Michigan, and Indianapolis, Indiana. If you're tired of dealing with expensive properties, difficult evictions, and disappointing cash flow, maybe it's time to start investing somewhere else.

Dating apps are for amateurs. Why waste time swiping right when you've already got a Section 8 portfolio full of single moms?

New York renters, I've got a question for you. If you plan on paying your rent every month, why would you have a problem with a landlord who makes it crystal clear that nonpayment leads to eviction? I'm James Wise from HoltonWiseTV, and I believe one of the biggest mistakes landlords make is failing to establish expectations before handing over the keys. If you're screening tenants for Section 8 rentals or traditional rental properties, you need to be upfront about rent payments, lease violations, and what happens when tenants stop paying. Of course, evictions must follow the law, and landlords can't just show up and throw someone's belongings in the trash. But here's the bigger question: Why would a responsible tenant be afraid of a landlord who actually enforces the lease? Whether you're investing in tenant-friendly markets like New York City and Los Angeles or building a cash-flowing Section 8 portfolio in landlord-friendlier markets like Cleveland, Ohio, Detroit, Michigan, and Memphis, Tennessee, tenant screening and professional property management can make or break your investment. At HoltonWiseTV, we help out-of-state real estate investors understand the risks, analyze rental properties, and build profitable portfolios. Landlords and renters, sound off in the comments: Is setting tough expectations smart business or going too far?

Think you need a mountain of cash to start buying Section 8 rental properties in Pittsburgh, Pennsylvania? Think again! I'm James Wise from HoltonWiseTV, and I'm showing real estate investors how to use seller financing to acquire cash-flowing rental properties without relying on traditional banks or massive down payments. With the right owner-financing deal, you can potentially buy Section 8 rentals with little to no money down, allowing you to scale your rental portfolio faster while keeping more of your cash available for additional investments. Pittsburgh is one of the markets I focus on, alongside Cleveland, Ohio, Detroit, Michigan, and Memphis, Tennessee. For out-of-state investors coming from expensive markets like Los Angeles, New York City, San Francisco, and San Diego, these affordable Midwest markets can offer opportunities to build serious rental income without spending millions. Whether you're looking to purchase your first Section 8 property or build an entire portfolio, HoltonWiseTV can help you find investment opportunities, analyze the numbers, and structure creative seller-financing deals. Stop waiting until you've saved a fortune to start investing. Contact HoltonWiseTV and let's talk about building your rental portfolio!

Detroit Section 8 rentals can be an absolute gold mine for real estate investors who know how to structure the right deals. I'm James Wise from HoltonWiseTV, and one of my favorite ways to build wealth through rental properties is combining seller financing with Section 8 cash flow. Instead of relying on traditional banks, investors can negotiate directly with sellers to purchase income-producing properties with flexible financing terms, potentially lower upfront costs, and strong long-term cash flow. Detroit, Michigan, is one of my favorite markets for this strategy, alongside Cleveland, Ohio, and Memphis, Tennessee. Whether you're an out-of-state investor coming from expensive markets like Los Angeles, New York City, or San Francisco, or you're looking to scale your existing rental portfolio, understanding seller financing can open the door to opportunities other investors overlook. I'll show you how to identify the right properties, negotiate better deals, and use Section 8 rental income to build long-term wealth.

In lower-income neighborhoods, tenant risk can be one of the biggest variables in the entire investment. That’s exactly why I often prefer Section 8 in these areas. When you’re investing in markets like Cleveland, Detroit, Memphis, Indianapolis, Toledo, Cincinnati, Columbus or Baltimore, the neighborhood matters just as much as the property itself. Section 8 can help reduce some of the income-related risk and bring more stability to rentals in areas where traditional tenant screening can get a lot tougher.

Everybody loves to bash landlords until it’s time to put 20% down, replace a furnace, fix a roof, pay property taxes, cover insurance, handle repairs and take the hit when a tenant stops paying. Real estate ownership comes with risk, responsibility and a lot of expenses people never see from the outside. If you think landlords have it easy, go buy a house, take on the risk and see what ownership actually looks like.

Sometimes the best real estate deal is not about getting the lowest purchase price. I was willing to pay roughly $30,000 over what I thought this property was worth because the seller financing terms made the deal work: low money down, a great interest rate and dramatically less cash out of pocket. That is the kind of creative financing strategy I use when buying rentals, including Section 8 properties. I work with out-of-state investors coming from expensive markets like New York, Los Angeles, San Francisco and San Diego who are looking for better cash flow in some of my favorite Section 8 markets, including Cleveland, Detroit and Memphis. The lesson is simple: sometimes you give the seller their price so you can get your terms.

This is the side of Section 8 investing most people never see until they actually become landlords. When a tenant comes into the office acting like this, the question becomes pretty simple: do you really want another year of this relationship? Section 8 can be an incredible strategy when you buy the right property, in the right neighborhood, with the right tenant and management system. We work with out-of-state investors from expensive markets like New York, Los Angeles, San Francisco, San Diego and other high-cost cities who are looking for stronger cash flow in markets like Cleveland, Detroit and Memphis.

If a rental property has been sitting on the market for 363 days, I don’t need to see the photos, inspect the neighborhood, or run the numbers to know there’s a problem—the price is too high. Investors coming from expensive out-of-state markets like New York, Los Angeles, San Francisco, and New Jersey sometimes struggle with this because Midwest real estate is all about buying at the right number. Whether I’m analyzing Section 8 deals in Cleveland, Detroit, or Memphis, the market ultimately decides what a property is worth—not the seller. If the price made sense, somebody would have bought it.

Eviction day is already stressful enough, but some tenants still find a way to make the situation even more chaotic. In this video, the landlord is carrying out an eviction while the tenant complains about her baby daddy and everything else going wrong in her life. This is the side of rental property ownership most new investors never see before becoming landlords. If you’re investing from expensive markets like New York, Los Angeles, or San Francisco and looking for stronger cash flow, markets like Cleveland, Detroit, and Memphis can offer opportunities—but you still need to understand tenant screening, property management, and the realities of operating Section 8 and other rental properties.

There’s no shortage of Section 8 properties, but I’m not interested in buying just anywhere. I like Section 8 rentals positioned near stronger neighborhoods, major employment centers, downtown districts, and areas that could benefit from future appreciation and gentrification. In Cleveland, that can mean buying affordable rentals near places like University Circle, Little Italy, and Downtown Cleveland—areas where values can be dramatically higher just a short distance away. The goal is simple: collect Section 8 cash flow today while putting yourself in a position to potentially benefit from neighborhood improvement tomorrow. This is the kind of strategy I use when helping out-of-state investors from markets like New York, Los Angeles, San Francisco, and other expensive cities buy in some of my favorite Section 8 markets, including Cleveland, Detroit, and Memphis.

Sometimes the best real estate deal is not the one with the lowest purchase price—it is the one with the best terms. I have roughly $4 million in seller-financed real estate notes out there, and in some cases I was willing to pay a premium because the financing made the overall deal better. That is something out-of-state investors from expensive markets like New York, Los Angeles, San Francisco, and Chicago need to understand when they start looking at cash-flowing rentals in the Midwest and South. In markets like Cleveland, Detroit, and Memphis, three of my favorite Section 8 markets, the right financing structure can be just as important as the price you pay.

Eviction day is never pretty, and this tenant had something to say about every part of it. My team is there to do the job, take possession of the property, and get the landlord back in control of their investment. This is exactly why management matters, especially for out-of-state investors buying rentals in markets they do not live in. Whether you are investing from New York, Los Angeles, Chicago, or another expensive market, having a local team on the ground is critical. Cleveland, Detroit, and Memphis are three of my favorite Section 8 markets because the numbers can still make sense when the property, tenant, and management are handled correctly.

Cleveland’s lead laws can feel confusing because the rules, procedures, and enforcement have changed repeatedly over the last several years. For landlords and out-of-state investors, the key is having a local team that stays on top of the changes so you don’t have to. That’s why we work with Pb Free Ohio. Zak and his team handle the testing, reports, compliance process, and ongoing updates so investors can keep their Cleveland rentals moving without trying to decode every new rule themselves.

Chicago landlords need to remember one thing: you are running a business, not a charity. If a tenant stops paying rent, you still have a mortgage, taxes, insurance, repairs, and every other expense tied to that property. Feeling guilty about enforcing the lease can turn a profitable rental into a financial disaster fast. This is one of the reasons I focus so heavily on landlord-friendly markets and properly structured Section 8 investments for out-of-state investors coming from expensive markets like Chicago, New York, and Los Angeles. The right market, the right tenant screening, and the right management strategy can make all the difference.

Evictions can get emotional fast, especially when a tenant realizes the landlord is actually following through. On HoltonWiseTV, we look at what happens when an evicted tenants start pleading for one more chance—and why landlords have to separate emotion from business once a situation reaches this point. For out-of-state investors coming from expensive markets like New York, Los Angeles, San Francisco, and Chicago, tenant management is just as important as buying the right property. That’s also why I focus so heavily on strong systems in Section 8 markets like Baltimore, St. Louis, and Indianapolis, where the numbers can work—but only if you manage the property and the tenant relationship correctly.

Buying a non-performing note for $14,000 on a property worth around $20,000 might sound like easy money, but a $6,000 spread can disappear fast when you’re dealing with foreclosure attorneys, court costs, delays, and the possibility of having to remove the actual owner from the property. This isn’t a normal tenant eviction where you might be measuring the timeline in months. A contested foreclosure can drag on much longer, and every delay eats into your return. In this video, I break down why cheap doesn’t always mean profitable and why investors need a much bigger margin of safety before taking on a foreclosure deal like this.

A lot of investors hear “Section 8 in Chicago” and immediately think inspections, paperwork, delays, and headaches. But that difficulty is exactly why so many investors never learn the system—and why the investors who do can find serious opportunity. Chicago has massive tenant demand, one of the largest housing authorities in the country, and the potential for stable subsidized rent when the deal is structured correctly. In this video, I break down why Section 8 in Chicago can work, what most investors misunderstand, and why learning the process can give you an edge in one of the biggest rental markets in America.

Four units might be the perfect setup for Section 8 investors because you can collect four separate rent checks while still keeping the benefits of residential financing. Once you cross into five units, you’re typically entering the commercial lending world, where shorter amortization schedules, balloon payments, refinancing risk, and different lending standards can completely change the deal. In this video, I break down why fourplexes give investors a powerful combination of cash flow, diversification, and long-term financing—and why they can be especially attractive for out-of-state investors looking to build Section 8 portfolios in markets like Cleveland, Detroit, and Memphis.

You can have a completely valid reason to evict a tenant and still create a huge problem for yourself by losing your temper. If you start arguing, sending angry messages, using insults, or saying something that could be interpreted as discriminatory, you may hand the other side exactly what they need to challenge your case. Landlords need to stay professional, document everything, and let the legal process do the work. Don’t turn a straightforward eviction into a fair housing complaint, discrimination claim, or expensive lawsuit just because you couldn’t keep your mouth shut.

You don’t need to build an entire real estate team from scratch just to buy and operate a Cleveland rental property. At HoltonWise, investors can pick and choose the services they need—from purchasing the property and handling the transaction to inspections, insurance, lead paint compliance, and ongoing property management. Whether you want us involved in one small piece or you want everything handled under one roof, the choice is yours. This is especially valuable for out-of-state investors from markets like New York and Los Angeles who want exposure to Cleveland real estate without having to coordinate five different companies from hundreds or thousands of miles away.

This Section 8 inspection was absolutely insane—and it’s exactly the kind of thing out-of-state investors need to understand before buying rental property from thousands of miles away. Investors coming from expensive markets like New York, Los Angeles, San Francisco, and other high-cost cities are constantly looking for better cash flow in places like Cleveland, Detroit, and Baltimore, three of my favorite Section 8 markets. In this video, I break down what happened during this inspection, what landlords need to watch for, and why having the right team, process, and expectations matters when you’re investing out of state.

Most landlords aren’t wealthy corporations or Monopoly-style millionaires—they’re regular hardworking people trying to build a better life, create financial security, and leave something behind for their families. The problem is, a lot of new investors jump into rental real estate without understanding how difficult tenant issues can become when things go wrong. That’s why knowing your market, screening properly, and building the right management systems matters so much. In some of my best Section 8 markets like Cleveland, Baltimore, and Memphis, investors can still find affordable properties with strong rental demand and attractive cash flow. For out-of-state investors looking beyond expensive markets like Los Angeles and New York, I also spend a lot of time analyzing opportunities in places like Detroit, St. Louis, and Kansas City where your investment dollars can go much further.

A lot of new landlords think being extra nice, giving tenants second chances, and overlooking red flags will somehow make them better operators. In reality, successful Section 8 investing requires strong screening, clear policies, consistent management, and understanding how to protect the property and the cash flow. In this video, James Wise breaks down why inexperienced landlords often get burned and why professional systems matter, especially in affordable Section 8 markets like Cleveland, Detroit, and Memphis. For investors coming from expensive out-of-state markets like New York, Los Angeles, San Francisco, and other high-cost cities, the lower entry prices and stronger cash-flow potential can be attractive—but only if the property is managed like a business from day one.

Section 8 investing can produce strong cash flow, stable rent payments, and long-term tenants—but only if you understand what actually happens behind the numbers. HoltonWiseTV shows you the realities of owning and managing Section 8 rentals, including rent increases, tenant placement, inspections, turnovers, repairs, compliance, and the day-to-day management that investors need to be prepared for. For out-of-state investors coming from expensive markets like New York, Los Angeles, San Francisco, and other high-cost cities, markets like Cleveland, Detroit, Memphis, Baltimore, and Pittsburgh can offer dramatically lower entry prices and stronger cash-flow potential. The opportunity is real, but so is the work required to operate these properties correctly.

Eleven years ago, I wrote The Ultimate Guide to Grading Cleveland Neighborhoods on BiggerPockets because investors kept asking me whether a neighborhood was “good” or “bad.” I still don’t think that’s the right way to look at it. Real estate investing is about risk versus reward, and the neighborhood that makes sense for one investor may make no sense for another. That’s why I grade Cleveland neighborhoods on an A-to-F scale. In this example, we’re looking at a high-D/low-C area that I personally like for cash flow and believe is one of the more promising C/D-grade parts of the Cleveland market. I may not choose to live there myself, but investing and living are two completely different decisions.