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. 

If you ask the manager to justify a fee and he starts hemming and hawing, move on or require them to remove the fee.

If you don't get access to the property before closing it can be tricky but if there are recent photos online or you can walk through before and take your own then it is much easier.

Focus on what matters, not on things that have nothing to do with what drives the desired  results.

LOne common strategy is doing a cash-out refinance on one of your rental properties to tap into the equity.

Fake income documents are easily purchased online, and inexperienced screeners often miss red flags.

I have an STR and previously did not allow pets on our property out of fear that they would destroy it. 

It really is a minefield out there.I know everyone likes the convenience of the web, and they are tired of hearing it, but this really is a business based on relationships, not online anonymity.

Is it an official inspection or some notes on paper? 

It is tax free in the sense that you will not owe taxes today on the cash-out.