@Peyton LaBarbera you're not going to find or get a lot of info on SFR properties.For apartment buildings, owner's agent will typically provide a glossed up Pro Forma.

All that aside, this is my first investment - what should I be asking for from current owner?

They have so many great resources for owners and the community of hosts, property managers, and other vendors. 

The new owner has lost his job and will relocate for a new one.

Can owner choose contractors?

Permits: I think you should look into Poconos Association of Vacation Rental Owners - they are the STR owner's "lobbyist" for regulation in Poconos, and are spearheading the meeting with the township on the 20th.

The owner of that property did not have insurance because the they believed it was a waste of money if the house was paid off. 

App_mode=Displ...197.172    Interest rate; calculation and minimum.(1) Real property taxes shall bear interest at the rate of 18 percent per year from the date of delinquency until a certificate is sold [...]Translation: Property owners who are delinquent on their taxes, for which a tax certificate (i.e., tax lien) is sold at auction, are charged 18% per annum.197.432    Sale of tax certificates for unpaid taxes.(6) Each certificate shall be awarded to the person who will pay the taxes, interest, costs, and charges and will demand the lowest rate of interest, not in excess of the maximum rate of interest allowed by this chapter. [...]Translation: Florida is a bid-down interest rate state. 

We were able to provide an answer to the City's need for affordable housing and deliver an amazing 3/2 Ranch home on a sizable lot for a local owner-occupant.

I'm a co owner for a moving company.