shouldn't be too hard
I would love to fly in Italy!
Companies usually hire in the spring but it won't hurt to send out resumes soon. Lots of companies here in Canada operate R44 and AS350 and with a bit luck you can find a visa sponsor. Canadian Helicopters usually does sponsor quite a few Europeans every year but they ask for 1500 hrs so it depends how many resumes they'll get.
You can also look up the immigration website and see if you would qualify for permanent residency (like a green card).
PM me if you have any specific questions.
ciao