Thanks for all of the recs, Highland Parkers! 

I've had a few requests to share the list, so here are the responses I received:

“Highland Park resident Tim Stavenger, 412-661-4925

 

Kevin Wolf, a young college student who paints for a local contractor, is an excellent painter. Kevin painted box gutters for me last year and I had a great experience with him. His number is 412-728-2266.”

 

“We used Andre McKelvey of 5 Star Trademan at our church!  Did a Great job! 412-452-1536

 

“Paul Daugherty and his wife did a great job for us a few years ago and live in the neighborhood. (you can see them working on our house in Google street view: 1355 Heberton St). (412) 362-9517

 

“Jeff Carson is amazing and is very, very, reasonable. He painted our house last summer (6051 Grafton ) and we could not have been more happy. His number is: (724) 205-3619

 

“We used Ernie Dettore from Forest Hills -he does excellent job, dependable and trustworthy -family business and best rates we got in our search! 412-715-4049

 

Cyle Dowling and his cousin Mike Browning. 810-444-0010”

 

“We had our house painted (also brick w/ just trim to do) by Dan Hinchman, with Hinchman Contracting.  He did an excellent job and was especially helpful in identifying a couple of areas on the soffit that needed repaired (we don't get up that close to it most of the time!). His contact info is dhinchman@verizon.net, or 412-337-2672.”

 

i used rick at ultimate custom painting (lives in morningside) when i painted my house last year. they were great”