I've been lurking on this site for a long time, I thought I could help you out on this since Italy is where I live.
So, starting from your first post:
- skate scene in Italy is pretty good, expecially in a big city like Milan. The level is generally really lower compared to the states, but oh well! From my personal experiences skaters here tend to be nice and help you out, expecially if you come from another countries, just don't expect perfect english, we got some troubles with it hahah.
- Best city to skate I'd say Milan again, a lot of spots and some cool parks even though I don't really like to live there because it can be dirty and caotic sometimes. But then again, if you don't like it, you just have TONS of other cool cities at just 2 hours train ride, you'll love it, the two times I've been to the states it was all spread out and shit, here with a 8 hours trip you can virtually go anywhere you want, even abroad.
- I personally hate public transportation service here, but it's cheap and you don't need to get a car or being stuck in traffic for hours
- best thing about italy? there's much right there. Food, art, history are on top level in the world, and girls are nice here, just tell em you come from US or whatever hahah
- Decks are like 50 euros, expect skate related stuff to be more expensive than in the US
- In Milan there was a sick indoor park called Trinity. From what i heard it's gone now, and it's a total bummer. There's lots of stuff outdoor anyways, and winter here is not too bad.
- Skateshops: in Milan you got Treesse, that got a lot of stuff but it's like zumiez in the US you know, no skater owned and assistents tend to be really annoying. There's a cool skateshop skater owned in milan called Contest board shop, never been there though, but they will help you out for spot directions too im sure.
glad i could help, ask if you need more, in september im moving to milan for university so who knows!