Hermit Thrush, from Brattleboro, specializes in sour beers - so if you can find some of that on tap, I'd definitely check it out. I'm more of an IPA Girl myself, but my ski bar at Mt. Snow usually has a good assortment of local sours, so you won't have to look far.
Demo-ing at the hill is going to be your best bet to making sure you're properly kitted out for whatever the conditions are on the mountain. Biggest adjustment is going to be that you will be skiing on stuff that might get roped off if you encountered it in the west. Your demo gear is going to be tuned with moderately sharp edges, though, which makes a huge difference. They probably won't have it REALLY well tuned, which means that you're not likely to slice yourself on your edges but you probably shouldn't handle your demo skis with your bare hands. Totally not joking about that. Anyone who skis here intensively tends to keep their edges sharp enough to take the skin right off if you brush up against them. Test the edges on the demo skis and if they don't feel like sliding your hand along them would be a bad idea, find out if you can get them sharpened up a bit. The people working them demo desk should not flick an eyelash at this request.
If you make Waitsfield (or Warren, etc.) your home base for Sugarbush, Killington is just a hop skip and jump down the road and would be an easy-peasy day trip from there if you want to mix it up. If you want to go to Killington, though, you should probably start a separate post with Killington in the title, because there's all kinds of secret intel about where to park, and how to access the ski area that can be a make-or-break in the quality of your day. I don't ski at Killington at all, but I know that there are a bunch of Divas who do, and they'll be able to advise you on this.
There are a lot of great restaurants in the Mad River Valley area (where Sugarbush is). That's also Beer Central for Vermont. Used to be mill towns up there, and when the jobs left they were becoming derelict until someone realized that all that industrial space would be perfectly suited for breweries and distilleries, the state sunk some real money into it, and now there's a whole Beer Tourism scene there. Also, it is absolutely gorgeous, classic New England scenery.