I do Tuckermans every April (usually first weekend) with a decent sized group. I missed last year due to the crappy winter and injury, but I personally would not do the Ravine in winter. The Sherburne trail would be great after a nice dump though. You can take the Tuckerman trail up, which is groomed, and ride the Sherburne down from HoJo's (close to 2000 vertical feet). You can also mess around in Hillmans highway, but I have no experience there. I usually do the lip in bowl, but I take the advice of the day from the ski patrol. I finally have a helmet camera, so I hope the weather is good this Spring.