Hello and welcome, I am also 37, I live in the Uk. Like you I have spent much of my life trying to think of my bright idea. The problem I have is trying to commit to any one thing. It looks like at least you have tried to give different things a go and I commend you for that. Keep it up you will get there! In terms of places to live, I think everywhere has it's own good and bad parts. I have spent time in Italy, the people there are lovely but they have some enormous fiscal issues in the country.
RE: The road to location independence