I live three months a year in Ragusa. You will not find IT work (in any small town), but the cost of living is very low. You can find four-bedroom apartments to buy for under 100k euros. Fruits and vegetables at street markets seem practically free compared to many places. Eating in restaurants is generally expensive, though.

You will need to learn some Italian because the level of English here is still very low compared to most of Europe. With your other languages, I'm sure you can be proficient quickly though. People here are very welcoming.

Start doing contracting online or something where it doesn't matter where you live and you'll do fine even if you're not making much. The median Italian income is only like 21k euros and many make much less and survive. Health care here is very good and nearly free for all residents.