it's not hard at all. especially if you speak english fluently. probably the cheapest way to go for housing for just the ski season would be employee housing, but you'd have to get a job there. as for nightlife, theres not much in keystone, but breck does pretty well. and look in the colorado forum, quite a few threads in there on this.
if u guys are planning on working for keystone, they will put you up in dorms close to the lifts for very cheap. keystone has two small villages and a few decent bars (goat, dos locos, snake river) Dillon is down the road and there isnt much there either, but breck is a fun place to party any time, and frisco can be good as well (both are 15-20 min away)
I prefer Brecks park, the only problem is the lines because the park is at the bottom. Keystone's is also good, but they are super close and easy to get busses to/from so it doesn't really matter where you live.
the park is at the base of the mountain at breck, so all the gapers get in the way and cause rediculous lift lines, where at keystone the park is off to the side away from the main base, and has it's own lift. as for park quality both are top notch, i prefer keystone cause of the lift situation and have two decent sized jump lines is good too if the weather gets nasty.
Like I said, the lines are terrible at Breck, so if you want to get the most good park skiing in then you should ski breck Tuesday-Thursday and Keystone Fri-Monday, and any holidays/college breaks do Keystone too. Really living in Breck is prolly a little more fun, but also more expensive.
I think I'm heading over next season. I'm from the UK and it'll be my first NA season.
Basically, the conclusion I've come too is that staying in Breck will be a better experience.
Working for the mountain will get you a free pass and some cheap accommodation, though i've heard it isn't all that good. Working for a shop or bar/restaurant will more than likely get you a free pass, then you'll have to find accommodation.
If you are heading over then let me know bro, as I'm going alone and will probably be looking to get a house and car if you want to split costs or whatever.