50KalItís always a dice game when it comes to skiing season. Everywhere will eventually have a bad season. The best thing to do is save as much money in summer/fall as you can, and pray for snow.
Yeah this is pretty true.
I think if you have a specific jib you want to work, or location you want to live base it off that and hope the snow comes.
Jobs start to go up in sept. Most go up in october. It depends on the type of job you want. Check indeed/simply hired or Vail etc. websites for jobs in those resort groups.
I would apply to multiple places and either go where you get a job, or if you get multiple offers choose the best one. Employee housing can be tight in the big ski towns. Make sure to ask if they have employee housing. Some departments hold down more rooms than others. IF you don't have any particular skills that make you a real asset for whatever job get in early. Good idea anyway but if you're going to be on the same playing field with everyone else, get in early.
Check craiglist etc in prospective areas. See what the housing market is like. Are you moving solo? Do you have friends that are keen? Obviously 2 or 3 br places are going to be way cheaper for you than a studio. Plan ahead in case employee housing isn't an option. Some massive resorts don't even have employee housing. Some have it but it's very very tight.