Ive been to HPD Section 8 office numerous times in person telling them all the incidents and all they seem to do is defer me to housing court. 

Taxes are reappraised every year and if it is not your homestead, your property taxes can go up without limit.You have to really know the market and not just what prices seem to be.

The legal aspects also scare me a bit, but that's mostly out of ignorance rather than knowledge of what goes into it.But since I've read a bit more it seems that hiring a PM might not be in my best interest.

Seems like finding out if the person hiring them has the right to sell a property should be step 1?

Tom seems to be extremely knowledgeable about tax laws. 

Seems like it has to somehow....

What they are asking for seems pretty standard in regards to receiving a loan.

Business to business non-disclosure is one thing of "buyer beware" that is sadly tolerated; business to consumer games seems less tolerable these days.

Based on the initial information provided, I agree with @Kristine Ann that there does not seem to be enough spread between the asking price and sales comp, considering the work that needs to be do. 

Poverty people seem to rely on food stamps.