Initially, I should mention that I think Max did NOT get that photo off his old computer files. He probably had an idea for a cute post today and at 3:00 pm he pulled out a bottle of booze and started chugging with the camera timer set. not that there's anything wrong with that.
Re the ski trip, don't worry about going directly from Wilmot "Mountain" (rather, "ice hill") to the west. I skied Wilmot maybe 20 years ago for my first time and couldn't stay upright. I went to the bar with my older brother's girlfriend, who also couldn't stay upright (on SKIS people, on SKIS, get your minds out of the gutter!!).
Next time I went was Winter Park, CO and got a ski lesson from my brother-in-law. Agree with Ryan to get a real lesson, not family, but he had taught before and was really good at it. Did fine on greens first 2 days and then went to blues on day 3, so you don't need to really have any skill when you get there. I think stay green until you think it's boring then graduate if you can. Don't jump a color unless you think the lower color is too easy. With the better snow, better runs and better teachers, going west is actually easier skiing than here.
Hopefully, this won't be you ...