Like said above op it can be a problem having your job tied to your pass and housing.
But as a fellow Midwesterner to Colorado, its really only a problem if your a shitty worker or have problems managing money.
I spent 6 winters in a row while working a mountain job and using the employee housing. Never once had a problem other than getting yelled at by ski patrol. Keep in mind I was living a frugal life cause all I wanted to do was ski. Cheap beer with mac & cheese. Especially my first couple winters. I was making shit pay compared to friends working in hotels, restaurants and bars. But I skied more than 50% of those service workers cause they were hungover or to tired from working til 3am. It's all about what you want to do.
Also keep in mind the days are gone where you could just call in sick and ski your mountain. With electronic passes your bosses know when your skipping work and skiing. I was always shocked by the number of stupid people think they can get away with this.
If your looking to ski a lot at a lifty job get on a 4-3 schedule if they allow it or work somewhere that has a night skiing shift. Otherwise get your job and housing lined up out of the resorts and buy a pass.
I would also say go farther than A-basin. Nothing wrong A-basin but there's lots of cool ski resorts with housing that are bigger and have better parks if that's what your looking for. Telluride, Copper, Aspen Snowmass ( I spent 8 winters here), Breck, and Crest Butte. Normally hiring for these jobs won't be til June- August. So don't sweat if you don't any offers til summer.
If you have the ability to head out to CO this summer and work anywhere a bit and you could probably find a affordable housing situation in Summit county. Plus you could just camp around on FS land til you landed at a spot.
Also this summer consider working as a bartender, server, hotel concierge or similar to where you live. Build up some experience and somewhere out west would pick you up fast. There is always high demand of service workers out west.