I’ll be honest, that building sounds like a piece of crap. Inspections are easy to satisfy if you keep the building up. First of all, not many building inspectors take bribes (even in Chicago). Second of all, the updates they ask for aren’t crazy. Third of all, if you think the building inspector was bribed, discretely ask them about it as if you also want to bribe them. You can find out.
It sounds like you have some issues that they let you slide on before. Maybe the old building inspector retired during Covid and now you have somebody who’ll actually enforce the rules. You have an old ass building with a bunch of old ladies in it. That’s exactly what a run down building is like.