It is never a good time to buy a house in the States, so you should do it right now.
I heard that Italy's economy isn't so good right now, and a guy like yourself can do well in any environment, so get on the escalator which is rising the fastest. Plus, Southern California has a climate which is just as good as Italy's.
Your biggest problem will be in getting the wife to move away from her family. That's why I'm not in SoCal right now.
Incidentally, if I were to move to Southern California, I'd either move to the San Jose area (for the money) or to the woods and vineyards just north of San Francisco (for the climate and nature).