I kinda want to poll the audience and see what y’all think, first about me and my financial past....I'm going through a divorce and a possible foreclosure of the marital home as I can't afford to pay the mortgage by myself and she is unwilling to provide her share, not the point though, we have agreed to sell the house but a payment hasn't been made in almost a year, I've put deals together in the past for us and one way or another she ends up not signing and selling.

I honestly see the commercial property status as one of the important things you will need to verify.

I kinda want to poll the audience and see what y’all think, first about me and my financial past....I'm going through a divorce and a possible foreclosure of the marital home as I can't afford to pay the mortgage by myself and she is unwilling to provide her share, not the point though, we have agreed to sell the house but a payment hasn't been made in almost a year, I've put deals together in the past for us and one way or another she ends up not signing and selling.

You may want to look into claiming real estate professional status if you qualify. 

And each of those would probably be a lot easier and less hassle to rent than either individual rooms or a single house set up for large groups.Adding kitchens and baths is a significant job but it might be worth it in long term value if you could upgrade the place to 'real' duplex status.   

Given the status of the building (non-paying tenant + eviction moratorium) you should expect to take a hit on the sale price. 

All real estate income/losses are considered passive unless either you or your wife may claim a real estate professional status.

I could see it might compromise pass through tax status, but I know very little about LLCs and don’t know if they are for me at this stage.

In Chicago you can look up the permit status for any address.

Their responsibility is reviewing scope in question and confirming the completion status of scope.I hope this helps.