City/Country - San Sebastian, Spain (Much of the info can apply to other Spanish cities).
Firsthand Experience - Yes, Lived here 2 years.
Cost of Living - 3/10 - Western Europe isn't cheap and San Sebastian is the most expensive city in Spain. Having said that, San Seb is still much cheaper than some other European cities like London, Paris etc. A room in an apartment is likely to be round 300-400 Euro per month and a 2 bedroom apartment 700-1200 Euro a month + bills (depending on how nicer place you want). I'm paying 1100 a month for a 3bdrm place.
Recreation - 7/10-10/10? (depends on your idea of recreation) - Tough to put a rating out of 10 because it really depends on what you're into.
If you're really into your outdoor activities like surfing, snowboarding/skiing, hiking, kayaking, cycling etc. Then San Seb is probably a 10/10 for you. San Seb is one of very few Euro cities to have a decent surf break in the city, and many of Europe's best surf breaks are within an hour drive north or south. Skiing/boarding is within a 2-3 hour drive away in the French and Spanish Pyrenees. There's loads of hiking options around and other outdoor activities. San Seb also has a team in the worlds 2nd best league (with the worlds best players) La Liga. Biarritz and Bayonne often play big rugby matches here.
If you're really into your partying and going out clubbing every night and to big concerts every other night then San Seb is probably closer to a 6 or 7/10 outside of Summer(10/10 in Summer though, a lot going on from mid June till Mid Sep). San Seb is fairly small (population of 180,000 more or less) and therefore the nightlife doesn't compare to places like Barcelona, Madrid or London. Outside of Summer bars are generally only busy Thursday- Saturdays (unless their is a fiesta on) and their isn't a lot of variety in the nightlife.
How Scary? - 10/10 - Very safe here, you're not going to encounter any problems unless you really make a big effort to go searching for/creating problems.
Poker Playing? - 8/10 - No problems with online play. For live play, the casino here offers most nights. The times I've been there has just been 1 table with it either being a sit and go or NL cash game. Games are very soft in my limited experience there but the rake is high. They also have monthly tourney's ranging with a reasonably sized buy-in, which I'm yet to play.
Getting here - 5/10 - The local airport is tiny and I think only fly's domestically, Bilbao and Biarritz airports are around a 1 hour bus trip away and between them they have pretty good links to the rest of Europe. Madrid, Barcelona and Paris Airports are roughly 6 hours away on a train and obviously have good links to everywhere.
Staying here - 10/10 for Euros, 7/10 for others. - Like everywhere else in the Shengen zone, those from non EU Western countries automatically get 3 month tourist visas on entry. To stay longer the main options are...
-Get Sponsored through your job (won't work for poker players obv)
- Get a student visa through a language school (pretty easy from what I've heard)
-Overstay (do-able from what I understand but obv not something I should recommend)
To stay permanently your best bet is to meet a nice Spanish girl and get a partnership visa with her or get married.
I also understand that if you live here 3 years and are able to prove it you are able to apply for Spanish residency.
For better info on this stuff check out this site..
http://www.spainexpat.com/
Other stuff -
Food - Great for the high rollers out there, more Michelin stars per capita than any other city in the world, 2 of the top 10 and 4 of the top 50 restaurants in the world in or near San Seb (according to restaurant magazine). San Seb also has the best Tapas (pintxos) here in all of Spain. Only thing San Seb lacks in food is variety, most of the food here is Spanish/Basque style, not many good Asian/Indian/Arab food options here.
Language - English here is OK compared to the rest of Spain, I came not knowing any Spanish and managed to survive (I speak OK Spanish now). Locals here also are happy to speak English if they know any (unlike 40km north in France). Having said that, the more Spanish you know the easier life is here, anyone looking to come here long term should make an effort to learn and speak some Spanish. Basque is also spoken here but I wouldn't worry about learning that since it's near impossible to learn and all the locals here speak Spanish anyway.
Any other questions let me know.