There should be something about needing a payoff letter.

@Justin Brin Yes, you can elect to aggregate your rental properties for Qualified Business Income (QBI) purposes, but once you do, you must continue to aggregate those same properties in future years unless there is a significant change in circumstances (such as disposing of a property).

Toss in a BRRRR strategy with a few other strategies and the potential to live mortgage free and cash flow when you move out of property is real. 

I have a lot of drive.

Also if he does have a home, can't get get a HELOC to borrow money to cover the rent?

So, tell a story of how you (or a fellow wholesaler) helped a seller out with their challenge(s).

@Adeel Makda there are a lot of great options in the Chicago area.

Through the early years I'd post a few times then go dark for months at a time, even into my early days of being an agent, always been hot and cold, in my postings. 

Would love a copy as well!

Cash flow will be a function of how much you put down.