You did not say why they do not qualify?

My basic philosophy is that if you can't handle the little things, then you can't handle the big things.

Do you own all of your rentals in Chicago?

It also depends on market conditions and availability of cash in the market, both of which will create more or less "meat" so to speak in the deal.

Make that call—future-you will thank you!

They give you 20-30 days to prove they are gone or cancel your insurance.

You might want to check with local credit unions or community banks, as they’re often more flexible with second mortgages. 

Not as walkable, however, as some of the neighborhoods that you have referenced here.  

I am happy to share some info on these sub markets if you like. 

(Or a lot if you're dealing with a scam turnkey company, of which, unfortunately, there are a decent number.)BRRRR is much more active, you buy a fixer as you note, oversee the rehab yourself and then either manage yourself or find a manager for.