Of course, they may go into "denial mode" on you and insist they just want out of their lease and even falsely claim their lawyer told them you had to let them out, etc., just to get what they want.

You insist you won't sell.As a teacher you have winter break.

I spoke with each tenant and they all insisted they weren't smoking in their units. 

And if you have financed the property the bank will insist on a certain minimum of coverage.

Should I insist on being on the deed? 

INSIST on videos or even ZOOM walk-thrus before paying.

Unlike with the many weed stores, this is not whack-a-mole or needle in a haystack because each OTA has to report and is financially liable.Booking.com and VRBO made it clear they weren't interested in fighting or getting fines and insisted hosts register or delist.Airbnb has instituted hosts, and now people are seeing a dialogue saying they must enter a registration number to continue (currently it has an option to "skip for now"). 

He insists there are violations from before we bought the property even though (1) the closing attorney said we got clear title and there's nothing about violations in the closing documents (2) the realtor said he wasn't aware of any violations from before we bought the house and (3) no violations appear when we checked online on the department of buildings website (this one: https://webapps1.cityofchicago.org/buildingviolati...)Now, this is an old house so some things are bound to not be up to the current codes.

Low wage earners, thus he insists on weekly rent. 

My inital thought is it would be fastest to to just resubmit against the original plans as most of the rewiew has been approved, but it was a red flag to me and when directly asked whether the application was expedited he refused to answer and insists that new application will have the self-cert, but the building person to say its not even possible.- shouldn't he know all of this?