I'm in the Mid-West and my local hill is a huge Chicago bus trip destination. So very small hill to start with, big crowds, and we can have very if'y conditions. I started riding 3 years ago at 42yr, and progressed quite well. Having fun just to be riding, there were days we bailed do to conditions but never crowds. Like I said would rather ride 6 of 7 days a week at times then 6 times a year at a good-great resort. I was able to get 30+ days on the hill last season even with our shitty winter we had.
You have a good plan, ride and get better and enjoy a real trip somewhere doesn't need to be cross country. We have traveled to much better resorts roughly 3 hour one way trip and had a blast. Wish I could afford out west but we try to take several local day trips to some of the better hills that we can get to.