Just some random thoughts from someone who's been there / done that (and still doing it):
1. When you start ski bumming your priorities should probably look like: great mountain, great skiing, and great people followed distantly by great job, survivable income, and a decent place to live.
2. If you do this for a few years, because you might like it too much and/or fall into a great job, then you'll find your priorities will change. #1 will be finding a decent place to live, #2 will be finding a great community, #3 is a survivable income, and then somewhere after all that is where the skiing falls. (Sure, there are exceptions to this rule, but it's how I think most professional ski bums come to view things.)
Therefore, do pay attention now to how well the mountain skis. You want to find a place where you can run out the door and get a couple of mindblowing runs in with just a few chairlift rides. So, places like Copper and A Basin are nice, Alta-bird is nice. Places like Steamboat, Keystone and such are harder. Your first few years you'll want to try to get a 100 days of skiing in. Later, you'll only care about getting 100 great runs in.
The next thing is people. Mountain towns are distinct from the type of folks you find elsewhere. I think it's important you go to a mountain town and not somewhere like Denver or Salt Lake City. Those are ok cities, but what you're looking for is a place that has TGR movie premieres at the bar, where it's ok to walk into the coffee shop with your dog, and where there's people named Biff America or Pigger and everyone knows who that is. There's plenty of time in your life to end up in an urban wasteland.
If I had to choose somewhere to go, it'd be off the beaten path. Somewhere like Silverton or Whitefish or Sandpoint or Bend or something like that. Maybe not as important if you're just doing a year because you'll think Frisco or Truckee or Vail is THE COOLEST PLACE YOU'VE EVER BEEN.
Arguably, employee housing... or even housing... isn't that important UNLESS you want your own place. Then it becomes difficult. If you don't mind sharing a two bedroom condo with four guys, you'll be fine.
With regards to insurance, most resorts offer some form of short-term insurance you can get, but you also almost always have to pay 100% out of pocket for it. We have a Blue Cross/Blue Shield program we offer (at least we used to, haven't looked recently) for $99 per month. It's like a $5000 deductible or something, but it's better than nothing.