If you can show verifiable statements of withdrawals and deposits, which shows you are playing poker as a job I think it should be fine. Alternatively you could be a student and study Italian at a very liberal pace.
From:
http://europa.eu/youreurope/citizens...s/index_en.htm
You have the right to live in any EU country for the duration of your studies if you:
are enrolled in an approved educational establishment
have sufficient income (from any source) to live without needing income support
have comprehensive health insurance cover there.
I would probably go this route, as learning Italian for a couple of hours a week would be useful during the time you are there anyway.
Next you need to find an '
approved educational establishment' which offers a course. I'm sure pretty much any college will have a course which is cheap and which takes place only a few hours a week and over a long period. Looks like the best option.
Don't ask for money from the Italian govt. Obv.
Finally, get comprehensive private health insurance.
You're good to go.