You didn't mention if you will be working with a company or perhaps U.S. DOD/Army/Air Force or Navy. With DOD you would have a SOFA agreement so taxes and gas are cheaper than on economy.
I was DOD overseas for four tours. First two tours I bought beaters in country and had fun but no reliability. Second two tours I brought U.S. spec vehicles without issues, a Toyota Avalon and Honda Element. In Germany there were Toyota and Honda dealerships so no worries. I still purchased a secondary local vehicle for job security as maintenance and accidents can leave you without a ride.
Yes, Italy can have some very small roads but also has autostrada (highway) and lots of amazing back country roads in Dolomites to drive, perfect way to adventure in your Passport like I did all over Italy, Slovenia, Croatia and Austria in my Element.
Realistically if you will live in big city like Naples or Rome, buy something small over there. If you are DOD/State Department and will be living outside major cities, bring the Passport and have fun. Parking was never a problem, you just might walk a little farther. Again if you are DOD/State then you would have access to USPS and lots of car parts businesses ship to APO....and how much heavy duty maintenance will need to be done in first 3 years of ownership? Any Italian garage can do basics and if you bring parts, they can repair just about anything.
If it were me, I would consider bringing...but I have a lot of overseas time driving around Italy. Here is Passo di Guau....Good luck!
