However, I'm looking a bit ahead when I will have access to rollover IRA assets that might be employed in a passive income scenario while also providing overall diversity to my entire retirement program. 

Chicago renters know the game and always  rental lease addendums be best looked over by a Chicago Lawyer before you start pissing off your renters.

@Daniel Raposo, really great to hear that BRRRR can be a reasonable strategy at this stage in the game for the right deal.

Lower price markets it happens for sure, but its a different game here. 

Lenders sometimes get in on this game too, alas (especially if it's new construction and you took the bribe to use the builder's "preferred lender" - that's the whole point of the bribe to use that lender!).

Rinse, Repeat.I am very new to the game, so like I said, take what I say with a grain...

That will tell you whether the property produces cash flow, or bleeds cash, a fundamentally important question.Assuming a specific amount of appreciation is a gambler's game.

Clearly, there is money to be made purchasing distressed properties, making minimal repairs, and renting them out to Section 8 and VA voucher recipients, but this doesn't necessarily help stabilize a community because the residents have no skin in the game.

Just wholesaling and making money no real game plan.

Great to hear that you're back in the game!