i am from frankfurt, germany and lived in austria, spain, boston and am now looking for a place around the northern italy and southern france.
spent 5 years in Vienna, austria and have strong pros:
safe, multicultural, great food, great insurance, everyone speaks english, you can find cheap rent, food and bars everywhere (with a little local help) decent spots, great parks, decent weather and stable good value job economy.
you can easily earn enough money to spend two-three months of winter on cheap holidays in the south and go to italy, portugal or spain, ...
BCN 4 years, nice city, skate mecca, weather is good but my big downside was that the drinking/drug and party culture is so tempting that it is hard to save up on the low minimum wage and it es extremely easy to get stuck there living month to month and not being able to save up, so had to force myself to get my shit together and move, now i can go there for cheap vacation without the danger of getting sucked into low minimum wage.
i love Lisbon, it is a bit grimy and has the bcn edginess but is packed with brazilian people and food, a very vibrant city and is so cheap, it is hard to believe, a bit trickier with english though, but you'll be fine. you shouldn't live in a country wthout learning that language anyways, in my opinion.
greece is paradise, so nice you might forget about skating completely because the shade of the olive trees is all you need and want for 6months/year
spent some great time in bilbao, spain which i liked a lot as a city, you can surf around the galician coast, it is quiet, safe, clean and culturally super interesting, nice spots too!
montpellier, france is nice too. good weather, young people, nice city to skate around in, has a little french mini bcn vibe.