We've been going to CB at Christmas several years now and will back next month.
Skiing- typically really good snow but last year was a little light, a lot more came later in the season. There is a decent amount of beginner/intermediate, but a lot of blacks. Base area has 2 main lifts, Red Lady goes half way up, collects most of the beginners, and can be a decent line. Silver Queen goes all the way up, only 1 easyish way down, not really a line. I like the back side with paradise express and no crowds. Painter Boy lift is the biggest choke point on the mountain, avoid if possible.
City-
Gunnison is the main city for the region and where your should do most of your grocery shopping. 30ish minutes from CB. I make sure to eat at Mario's pizza at some point each trip. Liquor store across the street from City Market is well stocked.
Crested Butte itself is a couple miles from the base, nice town with some good restaurants and free shuttle buses from town to base area. Small grocery store in town but expensive.
Mt. Crested Butte is its own town at the base area. There are a couple little convenience stores and restaurants but nothing great.
Rentals-
I've rented from the big shop at the base area, the Alpiner in CB, and Gene Taylor's in Gunnison. Pros and cons to all. Most convenient and expensive at base. Alpiner in CB is a Christy's store. Gene Taylor's is super cheap but need to factor transportation and return times in Gunnison.
Overall, mountain is a nice low key ski vacation with good amenities without the big crowds of Bruce/Keystone. It's a Vail Resort, so good infrastructure but you pay for it.
I'm happy to answer any questions that you may have. Email is username @ hotmail