Things worked out pretty well for me and some of it was luck. I happened to see an ad in an Irish newspaper for an au pair and, desperate for a job, I applied. Turned out to be one of the luckiest things I did. This took care of a roof over my head and money, and created an automatic "family" for me. They led me by the hand until I acclimatized to the U.S. - explained how taxes work here, how to open a bank account, credit history, stuff like that. They even helped get me my new job in Boston - put a word in for me.
I would recommend, if you don't know anyone in Italy (if that is where you intend to go) to visit beforehand - which sounds like you are going to do. Make a point to meet, talk and make friends with people. Express an interest in living there and ask about what you would need to know to relocate there. They are key to you finding your way around, getting a bargain rental to stay in until you figure out what is inexpensive and what would rip you off. If you know of any other people who are living close-by (friends of friends, distant cousins, anything) call them. Have them put you up for a week so you can go wandering about. Even if you know someone in a nearby country - call or write to them so they know you are going to be in the area. They could be a back-up plan to visit if things do not work out. You could get a minor job to keep you going but I do think your italian needs to be good.
When I moved to Boston, the first thing I did was buy a train pass and a map and I travelled on each line and got off at each stop. I picked where I wanted to live by looking around on my own and then purchasing a handy book called "Settling in Boston". It gave me information such as details on neighborhoods, post offices, how to get around, public transportation, what a tenant should know / standard apartment lease information, AMPs, TV, Phone, cable company information, where to register a vehicle, how to take a drivers test, how to register to vote, and loads of good stuff like that. When you visit Italy, look in their local bookstores and ask for a handy "guide" like this. It could be choc-full of information. On the other hand, if you were interested in tourism, how about applying to a local hotel for a job? As an English speaker you would be handy for tourists and it would mean that the hotel would have to teach and show you where to go, how to get there, and fast.
This is a site I found online about an
American family living in Italy
- not a bad idea to reach out to some expats for some specific information.
Read a couple of books like
"Buying a Property" to get some local insight. Not a definitive guide to use but to give an idea of the local customs and questions they expect of you when you do eventually want to buy something.
This is another handy little site about
Business in Italy and how to behave. There is a "Message Board" here where you can talk to like-minded people. Give it a shot.
Surf the net for more sites on moving, relocating and settling in to Italy
like this one
and
this one