Close to CA, tech and manufacturing job growth, 4th lowest property taxes that don't reassess on the sale, and no state income tax. 

Most title companies and closing attorneys these days want wires in my experience.

I live fairly close to the Poconos.

So if I buy his property today, I would have to add the $13,500 to my initial $4,500 to close the deal.

You pick the title company to close the transaction3.

First, even an STR that isn't rental arbitrage may in some cases be reported on a Schedule C rather than a Schedule E depending on whether you provide "substantial service".In the case of rental arbitrage, I believe the best and arguably only acceptable choice is Schedule C. 

I have kids and I know damn well they do not always close the curtain and I especially know when the tiles in the bathroom become uneven because of the water that gets trapped under them. 

But if you have commercial type loans, you may not have much of a choice and HELOCs do not count when you are under audit.

The homes come fully furnished, they all have pools/spas and will be rent ready from the day you close and often will convey with future bookings in place. 

It is never a binary decision it is a choice especially for a beginner like yourself.