My savings was completely drained from interest payments and surprise costs I had to manage, and lots of little costs that at the outset I believed this guy would cover (100 to mow grass, every two weeks).

While Section 8 appears to promise "guaranteed" income, the reality is quite different.Section 8 typically covers about 80% of the rent with tenants responsible for the remaining 20%.

Here is an article from Wolters Kluwer that covers the entities exempt from reporting.

If it's way out of whack with the market average, dig deeper.Debt Service Coverage Ratio: Key for nderstanding if the property's cash flow will cover financing comfortably.Historical Vacancy Trends: Especially in areas like Chicago, where local job markets fluctuate, knowing vacancy trends can help you anticipate rough patches.Rent Growth vs.

Talk to your insurance agent and be sure you're covered.

You could also offer to cover part of their tax liability through negotiation or encourage them to convert the property into their primary residence to use the IRS exclusion for up to $250K/$500K in gains.

You need sufficient rental income to cover your expenses, or you bleed money. 

Otherwise, you won't have the extra funds necessary to cover the rising costs of goods and services in the future.What causes rents (and prices) to increase?

The best and largest QI firms in America can have less than stellar regional or local representation.  

If the rental income doesn’t sufficiently cover the debt payments by their standards, they’ll limit the loan amount, even if the property is worth more.You could try a few alternatives:•Look for lenders who specialize in commercial real estate and have more flexible DSCR requirements.