When I talk with them we talk about Florida and North Carolina.  

His zoom calls are basically him talking to his buddies and he is very rude when you pose a question.  

I have talked to a few lenders and have a better idea of what would work best for us in this situation.

Feel free to reach out if you would like to talk more in depth! 

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

Have you had a chance to talk with your lender yet?

Also when you are under contract and get condo docs, make sure to read the meeting minutes (for the past year if available) they will indicate if there are any talks of an upcoming special assessment (which you don't want).

I wouldn't want someone to hold back, I prefer honesty and straight talk. 

I would do what @Mike Grudzien says and talk to a knowledgeable attorney on this.

Talk with the HOA.