Switching property managers seems like it was a smart move, especially with how much you and your wife had to step in before.Chicago definitely isn’t an easy market, but it sounds like you’re set up for better success moving forward.

I think deciding on a market is a really important first step. 

Nick is a sharp investor U may want to see if he will engage you off line for some deeper dive in methods for success 

. - which I suspect you're already inclined to do.You can also investigate various methods of pipe replacement / renewal that involve trenchless technologies, such as pipe lining, pipe bursting, or directional drilling.

Some recommend the STACK method also.

So when you buy your next property or use the brrr method, how do you typically finance it?

There is the negotiating step, and the closing step, followed by the moving step.  

Biggest thing here is they wants a house big enough for 2 separate living areas and house cannot have more than just a few steps to entrance and hopefully rear entry/etc.

House hacking and the BRRRR method are great for stretching capital efficiently.

I realize that the competition is one step, if not multiple steps ahead of me, and that is okay because I know that I can reach people who will say yes to me.