You could always look at teaching Italian or if your English is good enough teaching English. Don't expect it to pay a lot though. Before thinking of living there why not start with visiting to see if life there is really the way you believe it is. Keep in mind that visiting a place and living in a place are two very different things, but that will at least give you a peek at life there. You will definitely need some Japanese language skills and the more you have the better.
Whether someone, anyone, likes living in Japan or not really depends on them and their situation. It really won't tell you if you would like living there.
The above advice for a job, teaching languages, would be more suited for a short stay then a lifelong employment option, though some do exist. I would start small and if you really want to keep living there look for other, better, opportunities that will pay the bills and support a family if that is what you have in mind.
You didn't say this, but as a precaution I want to give you a heads up. If your intent is to go to Japan because of all the cute girls that you have seen in your favorite anime, you may want to re-think your reasons for going. There are plenty of cute girls but anime is not a reality. Also, many of those girls will likely not speak Italian and will likely have fairly limited English as well. Even if this is in no way part of your reasons for wanting to go there it will serve as a good warning to others who read this thread.
Hope this helps and good luck!