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Employment - most places you can find a job. Cost of living - will always be a factor and probably more expensive than where you live, since you will not know the best deals to buy things. Women will be hit/miss because you are a foreigner and are different.
For me the biggest problem was the weather and the food, alot of places in Europe have bad food and worst weather. This coming from a "canadian", yes are winters can be cold but at least we get sunshine.
I'd say most places you would struggle to find a decent job as a foreigner unless you are fluent in the local language. If you live in Western Europe or North America then most places you move to will be cheaper (assuming you don't move from one West European country to another). In my experience wherever you go you'll find a group of women who are very receptive to you as a foreigner because you're a bit exotic or different. Europe has such a vast array of food and a lot of it is good, think Italian and French which are considered some of the best in the world. Most places have warm summers so it's not all bad.
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For me it is something instinctive. Sometimes I go somewhere and just know instinctively that it's the kind of place I could live in regardless of the work situation,weather etc. I've been to cities which seemingly ticked all the boxes,like Barcelona for example,but I just never felt it and so never made the move.
Yeah I know what you mean, some places even though not perfect just give me a good vibe and I know I'll enjoy it there but others which seemingly have it all just don't feel right for me.
I guess my ideal places would be:
Warm but not overly humid and with occassional rain that wasn't torrential.
Freindly locals and girls I find attractive.
Cheap for accomodation, food and beer.
Easy to stay in for a few months at a time without having to leave the country or extend visas (or at least it needs to be easy).
Plenty of things to keep me occupied, not just a place with good looking girls as that would get boring.