The skate scene in Philly is the best it’s ever been IMO. In addition to the street spots everyone thinks of there are a decent amount of smaller skateparks that have been built throughout the city over more recent-ish years (in the Lower Northeast, Kensington/Fishtown, South Philly, West Philly, Southwest Philly) and a number of different cool DIY spots. Like someone mentioned, 9th and Poplar is a terrific diverse obstacle DIY, there’s a more lowkey (but still pretty large) DIY spot in Roxborough, a few in South Philly, etc. Obviously you also have FDR, the big semi-plaza influenced skatepark by the Art Museum (Paine’s Park), and there are also some indoor places to skate as well in both the city and suburbs with paid memberships.
In terms of areas to live for skating, if you have a car basically anywhere but the parking sucks in a lot of the denser, nicer, and/or more trendy neighborhoods. Things within walking distance to the Broad Street line and the Market Frankford El which are the two “subway” type lines are the easiest for public transportation (South Philly in the vicinity of Broad Street - East Passyunk and more eastern portion of Point Breeze, Fishtown/Northern Liberties northeast of Center City, some of the trendier parts of West Philly not far from Drexel/Penn, Spring Garden/Francisville in lower North Philly - Fairmount is another great neighborhood in that area but it’s a little further from the BSL but it’s easily skateable/walkable to Center City and stuff). There are also “regional rail” lines which go to further out neighborhoods in the city and extend far into the surburbs (they run less frequently though). East Falls, Manayunk, parts of Roxborough, parts of Mt Airy and Chestnut Hill are all accessible within walking distance of regional rail lines. Those neighborhoods are varying degrees of further from Center City and generally a little quieter than South Philly, Fishtown, etc. but there are still bars and restaurants and stuff to do. There are also decently walkable suburbs along regional rail lines which have some cool stuff going on - Jenkintown, Ambler (which has a skatepark, Lansdale (which has a skatepark), Conshohocken, Doylestown. Not as familiar with these areas but parts of the “Main Line” in the surburbs directly west of the city, also Media in Delaware County - many others too but I don’t know Delaware County or the Jersey suburbs that well…
Winters are essentially the same as NYC. Some of the spots are semi-covered like 9th and Poplar and FDR so depending what’s up with how the snow fell you can get lucky or once they’re cleared out they’re skateable sooner than other outdoor spots.
Kind of a rambling response. Hope that helped…