When you cut your counters make sure you use a fine-tooth circular saw, support the counter everywhere so it doesn't cave in your cut, cut it upside down, and put at least a 1" strip of painters tape down the middle of the cut line before you start to keep chipping at a minimum.

With just one rental, it's hard to build a relationship with plumbers, painters, cleaners, etc.

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.)