I guess my best bet would be to try and meet people who are currently in these roles and get their take. 

You bet I should have. 

NONE of these are safety or habitability concerns...NONE of them jeopardize the integrity of your investment.....

Yes, you are responsible to make it habitable.

You have to remember many of them don't have that kind of money laying around especially with Christmas only a month away.I think your rent might be too high as well.Your best bet is to get a property manager in there pronto and let them take care of it.  

I'll bet you a spotted owl BBQ sandwich that he is simply a squatter.

Cash flow month over month but very low property value seems to be a better approach East Orange is a better bet, sounds crazy but i know investors that purchase cheap East Orange, rent to section 8 and cash flow strong.

Theres also a duplicate trash bill at like $60 that I was hoping to have removed, but I don't think it is happening even though the attachments to both bills of the exact same amount are the exact same invoice date and price.I'm just looking for advice since she is clearly playing hardball and seeing what she can get away with during the transition with regard to betting that I'm either a pushover or won't bother with legal action over only a couple grand.  

Farmers paid the difference for the month tenants were there during repairs but not the remaining 1.5 months for which property was not habitable because of repairs.

Many habits of the PM we found troubling, like the way they wanted to show the property to 'everybody' qualified or not, and charge us even it the candidate never showed!