it will be easier for you to find a place to live around the holidays than it will be to find a decent job. I'm never really looking for a place to live that time a year, but I always see people coming in to town around the end of december and finding a place (even though everyone is always like "oh, there's nowhere available - that's bullshit).
but as I said, finding a job is the hard part. You can always throw your name into the hat at the hill, but there's no guarantee they will hire you, and in town the options are pretty slim, not saying it's impossible, but I wouldn't hold my breath. Not sure what their deal is for next year, but you could maybe try to contact the hill, tell them when you are planning on arriving in town and try to get a volunteer job, so you get your pass for free, which will give you a bit of extra coin and maybe allow you to not need a job? It's an option.