I have a partial team in place for Indy: property manager, handyman, painter, roofing company in place, no contractor (yet). 

And hire a real painter next time :-)

Then you'll also want to have copies of invoices that you've received (and paid) to any repairmen, painters, cleaners, etc., with proof that you paid them  (cancelled checks, credit card statements, like that). 

Get a painters jumpsuit/coverall.Definitely get a bug company involved. 

What about areas in Westmoreland County like Jeannette or Latrobe?

As you develop relationships with service people (habdymen, painters, etc.) make connections and be helpful. 

If you use these painters again maybe tape a sheet of paper to the no paint areas that says¡Sin pintura!

(See YouTube for The Idaho Painter for how to do the tape/caulk trick.)

Is that work the carpenter or the painter?  

There's so much competition that you'll hear from buyers over and over "Sorry - I just found out that my mother's babysitter has a dog walker whose 2nd cousin's house painter has a 3rd cousin that's a Realtor.