Paris has also crappy weather. Nice summers, but cold winters. So you can cut that of your list too Although I guess the winters are softer then in Estonia :|
If you're drawn to London but not so keen on big cities I suggest Cambridge - international atmosphere, cosy, housing (at least rentals) are easily available and it's quite easily the hippest city in Britain, outside the Camden Dock area of London of course... I'd be worried about getting into America - they're incredibly tight-arsed about immigration. I dunno if estonia is in the EU, but if it is you're all set for European countries - immigration is about as easy as showing your EU passport!
....well where im moving after highschool is either camp zoe, in salem missouri, or sanFranciscio which i think has changed alot so...either one........or california some where...i dont kno where ever you feel like moving you go for it