OvertheHillDiva,
I am old and I hiked that sucker last year. Went to the top of Hillman's with all my gear on my back. That was the physically hard part. It is doable for us oldies, if you are willing to be the slowest person going up. I had one companion as slow as me, and we stopped often. It took us forever to get to the top. But the view was constantly amazing on that sunny warm day, and being passed by young folks didn't bother us. We rested quite a while at the top before coming down. Skiing down is another story, however.
So if you're fit, and willing to do it, I'd suggest going for it. You can bail anytime the weight on your back gets too heavy, or your endurance just fades away. Just ski down when ready, or worn out.
It was bumps the whole way, but soft ones, all corn. I think I went at the end of April. Doing it on icy snow would be a do-not-fall-or-else-situation, not for people likely to be weakened by the long hike like me.
I didn't ski Tuckerman Ravine, only Hillman's. I walked up to the ravine the next weekend sans skis, and the hike up seemed much easier without skis and boots on the old aging back. That's another option - hike up without skis, but with lunch, to watch the younguns. It was quite a show there at the base of the ravine. Kids were on sleds, there were dogs, picnics, people having beer parties, amazing.