So be careful and make sure you interview the Expediter and that they have had success in obtaining the Letter of No Objection.As far as evidence that you need to gather, look up your buildings TAX Class.You will find it here: Building Information SearchHere you will see something that looks like this:NOTE that while this is a Dept of Buildings Web Portal, what I have circled in RED is the Department of FINANCE Building Classification.You may not have a CofO, but the Dept of Finance maybe taxing you as a 2 Family.

I am from the Chicago area as well.

Electrical as well but needs updating.

Try to track days on market and price trends to see how well an area is selling.There is a housing shortage in general, so every house will eventually be a home.

On top of the the borrower most likely owns it outright or has a small balance left on the loan.

And they do a fantastic job on the inspection, report, and in-person summary as well. 

Given its age, we’re planning for a roof replacement and two new AC units within the next few years, which we estimate will cost around 15 - 20k in total.Our single family rental, built in 2020, is newer, so we don't expect major repairs anytime soon.On average, the duplex runs about $400–500 per month in maintenance and repairs (including significant repairs like AC replacements), whereas the SFR averages under $100 per month.

Sounds like a cool plan.Welcome to BP!

Maybe if you really like these guys and their work...and feel that they honestly got in over their heads, you could throw them an extra $500 just to appear 'nice'.

Its as important in my industry (Logistics) as well.