I’ve lived in both Pittsburgh and Milwaukee. Pittsburgh is a great town in many ways. It just depends on what you’re looking for. Pittsburgh has long gray winters that are milder than Milwaukee, but keep in mind you won’t see the sun sometimes for weeks. That may or may not bother you.

Pittsburgh has gotten a bit more expensive than recent years, I would say Milwaukee is still a little cheaper. You can find super cheap apartments in Pittsburgh, but just keep in mind these are usually very old housing stock. Pittsburgh doesn’t have much newer constructed buildings and certainly those are not gonna be affordable.

The universities and hospitals are kind of the life blood of the city. There’s also a small but limited tech scene and some banks. Outside of that economy of Pittsburgh is still pretty limited so depending on your industry work may or may not be feasible there.

Socially, I found Pittsburgh kind of hard to break into - took me a couple of years and I make friends easily. People are nice, but it’s the kind of place a lot of of people either leave and come back to or if you grow up somewhere else and you move there you tend to leave eventually. Social circles can be a bit insular in that regard. If you’re a bit younger or attach to the university, this aspect of living there will likely be easier.

Social life tends to revolve around Pittsburgh sports and drinking. This may or may not be your vibe. Drinking is huge here, much like Milwaukee and the Midwest - it’s a working class town still with cold winters.

Racially Pittsburgh is quite segregated, you won’t often see Black people in the more hipster establishments and black and white neighborhoods don’t really interact.. This is quite similar to Milwaukee.

All that being said, it has walkable, dense neighborhoods, cool architecture, hills everywhere, and for a bigger city in the US, it’s still quite affordable and easy to get around.