If you do drive to Italy, be prepared to rent/buy snow tires or chains. You could get lucky and not need them, but if you're on the passes in the mountains without the right equipment, the fines & tickets will be very expensive, not to mention unsafe in your new ride. Europe has pretty strict rules, and as the driver you have to be prepared.
That said, just spent 2 weeks in Italy, including some skiing in Courmayeur. Totally great, totally worth it. Fewer tourists (except in Rome), so it was easy to see/do anything.