It gets fairly rural, fairly quickly, and I feel like we drove past a dozen or so state parks and campgrounds on the way back to I80, so I can't imagine you'll have too much issue finding a place that will work. As long as you "tow" something and can drop it, you'll be fine to get around the city with a truck too, though I will say, many of the roads, especially on Coal Hill, are SUPER narrow and tight. I got confused on one turn where the GPS said to turn left and I literally had to look out the window, essentially behind me, to see the street I was supposed to turn onto.
There are lots of museums, parks, monuments, etc. in Pitt that are easy to find and spend some time. There are also some historic neighboring towns, like Braddock, that have lots of history that you can literally park next to and explore (they did a cool job incorporating some of the abandoned steel mill machinery into the aesthetic and design).
He loves all thing 90's (my daughter does too)... they were born in the wrong decade! He had a Biggie shirt on in Cedar Point and had a few "great shirt" comments while waiting in line...
