Tuckerman's must be done at least once, after that you will want to come back as much as possible. Conditions can be a little sketch, sometimes you get an icy hardpack, but I still find it fun to hit it when it's hardest to ski. Hitting the cliffs and cornices on the lip is sick when there's good snow. If you go before April, be prepared to deal with avalanche conditions; after April, crevases and sink holes.
www.tuckerman.org
Don't wait to do it though, it's sick.