38 here. I nearly always roll solo although there is usually someone I know at the local parks. I've been rather tranny/park centric for the past decade but recently I've been trying to get some street back. My ledge and flat skills are rather embarrassing but honestly I've gotten a little bored of hanging out with old dudes doing frontside scratchers and stinkbugs. The problem with the more street like parks is that the age spread between me and the next oldest person is usually 18+ years.
The main reason I don't skate real streets so much is time constraints and the hassle of getting kicked out. I'd be happy if I had a spot with a manny pad, 3-stair, and ledge that wasn't a bust.
Just got over an injury, which thankfully doesn't happen that often but is something I can afford less and less these days because of day to day responsibilities. Guess that's in the back of my mind now.
Around here we still don't have a big, well rounded park. The old guys just want vert even if all they plan to do are the aforementioned frontside scratchers and the younger guys probably would be happy with just ledges and rails. I like a mix of bigger walls for speed, smaller hips to float, pryramids and euros that need to be ollied, small rails, a few easy QPs, a few super tight QPs, etc.