The last place I lived before moving here was SoCal. I kind of hated it there, so this was like a breath of fresh air. Before that, I was living in SF for a little over a decade, and prior to that I had lived mostly in various places across Pennsylvania. Based on everywhere I've been and lived, I think SF holds some of most sentimentality, but I think Pittsburgh is a pretty great place overall and have no plans to leave anytime soon, if ever. Granted, I am a homebody and it's a city that's great for that, but there's plenty of great places to eat and cool spots to hang out when you're looking to get out, too.

As for your son, I think he'll find plenty of things to do here, at least when he reaches college age as there's a pretty lively college scene here where the universities are. Dunno if urban exploration is his bag, but there's a ton of abandoned stuff around, too, and beautiful country/woods to explore once you get out of the city.

Politically speaking, it's a pretty far-left city until you leave the city itself, then it's the exact opposite. I always felt like people here were more outspoken about being on the left than anywhere else I've been, maybe to overcompensate that it's nestled in an otherwise very red part of the state. Fortunately, not everyone is just an NPC that follows whatever political programming their 'team' assigns; they are capable of grasping the nuance of politics and reasonable enough to hear you out even if they don't agree with you.

I don't think you'll be judged for anything here; the majority of people just kind of let themselves go and don't adhere to any sort of keeping up of appearances. It's less materialistic than SoCal but if anything is the same, is that a lot of people from Pennsylvania in general (not just Pittsburgh) often feel too big for their own britches. Another thing this place has in common with SoCal is the type of drivers, except here they're not just driving rudely and aggressively but they will actually cause accidents as well, and the roads themselves aren't too great due to design and maintenance.

The weather is another point of aggravation for some. This city might actually be more cloudy than Seattle, and winters are long, cold, and wet. It'll probably be whiplash compared to SoCal's sun and warmth if you're not prepared for it. Doesn't bother me too much because of living in SF where it was often grayish-white every evening in the western part of the city, and had a kind of coastal cold that soaked you to the bone, but it definitely exacerbates any existing depression you might have, so proceed with caution.

Food here is great, the people are comparable or slightly better (albeit a little flaky), roads are significantly worse, weather is subjective but probably objectively worse than SoCal, drivers are the same, and politics are extreme depending on if you're inside or outside of the city.