HoltonWiseTV Highlights (48)

Retail demand is drying up all over Chicago, but that doesn’t mean a property is dead. In Chicago you can run into a deal where the retail space is functionally obsolete, yet the numbers still work because of Section 8 cash flow. You’ll see how guaranteed rent, massive tenant demand, and the right unit layout can turn an “uninvestable” mixed-use building into a strong income property, and why investors who understand Section 8 can profit where traditional retail buyers can’t.

Most homebuyers in Chicago are chasing the same clean, pretty houses, and that’s exactly why Section 8 investors shouldn’t be. The best Section 8 deals are often the properties owner-occupants pass on. Less competition leads to better pricing and stronger cash flow, and what really matters to make these rentals work long-term. If you want to buy smarter, avoid bidding wars, and build stable income with Chicago Section 8 properties, this strategy is a game-changer. Subscribe to HoltonWiseTV for more tips on making money investing in Chicago real estate.

One of the biggest advantages of Section 8 investing in Chicago is something most people don’t even realize, your rent is guaranteed and approved before the tenant ever moves in. On HoltonWiseTV, we break down how Chicago’s Housing Authority locks in rent, why that upfront payment security is a game-changer for cash flow, and how smart investors use it to confidently scale rental portfolios in one of the strongest rental markets in the country. Subscribe to HoltonWiseTV if you’re tired of chasing tenants for rent and want stability, demand, and real numbers that actually work.

This is one of the hardest sides of Section 8 investing in Chicago that nobody wants to talk about. If you're seeing this eviction clip, it's because you are an investor in Chicago who is interested in Section 8 housing. When you're a Section 8 investor, you'll see things you never thought you'd see. When you're dealing with Section 8 tenants, you're going to see people living hard lives. You'll see poor parenting. You'll see people making terrible decisions. Subscribe to HoltonWiseTV for a real look at the responsibility that comes with Section 8 housing, the flaws in the system, and why Section 8 is such a tough business to be involved in.