I'm italian, I live in Torino (Turin)

Milano is really hard to ride, the only nice thing is that the traffic is so congested that sometimes ALL the cars are not moving at all.
Rome is no better and it's built on seven different hills.
Tuscany is good.

If I had to live somewhere in Europe, my first choice would be Copenhagen, second Amsterdam, I would also check Germany and Switzerland, I dont' like France or Spain even if Barcellona is a really nice place to ride and party