I strongly advise anyone purchasing an old house to flip to ensure they have a clear understanding of the condition of the home's drainage system.

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

I would strongly encourage you to buy properties that cash flow or break even.

Hey Rafael, as someone who's been investing in Florida for 20 years, especially in Tampa, I'd say you can’t go wrong with focusing on this market—it’s got strong appreciation, great rental demand, and tax-friendly opportunities.

There is still strong demand for Austin area housing.

The S8 portion will very likely arrive like clockwork on the 1st of the month.One strong motivation for the tenant to pay is they lose their voucher if they are evicted or leave owing you a balance.

If they’re late a third time, you have a strong case for eviction for habitual non-payment—without risking the tenant showing up at the 11th hour with the money.For your specific circumstances, with only a partial month behind, I would guess there is a decent chance they can come even on rent and it would be a waste of your time.

Risk & Due Diligence – Ensure the deal has strong equity, a solid exit strategy, and an experienced investor before funding.

The rent-to-price ratios in many neighborhoods are strong, and the city’s population is finally growing again after decades of decline.One thing that stands out to me is Detroit’s median home price—around $95k—which is far below comparable cities of its size in terms of population.

Just make sure the appreciation rate is strong where you buy.