Where in Italy? I've always considered moving to Italy for the beautiful landscapes, food and the people, but salary as SW was always what kept me from it.
I've lived there. Best to have US clients, except you still get paid in $, aka 0.8 euro on the dollar
Alto Adige (South Tyrol),
Which is one of the economically strongest regions of Italy.
Lots of mountains (well, the Region used to be part of Austria, and people speak mostly German and Italian here.
I don't even think self-employed web developers have an easier time, there's just too many, it seems...