To Waumbek's point:
Weather should play a role in you planning. I dislike seeing the rain/snow cancels on many AMC trips. I understand it, if hiking with strangers who's ability I only know from a 5 minute phone call, I wouldn't be in any hurry to find out if they embellished their experience. (personally when I've coordinated a hike, I 'd rather hear about the times people turned back, not that you have done all the 4k.s That could just mean you went out a lot one summer & early fall because you had lots of spare time that year)
When I solo, often times I have two or three places I am thinking about, especially in winter. A calm warm day will send me someplace above treeline.
A more typical day may send me someplace with a brief stop on a bare summit like Pierce, Garfield or Liberty (places I've also been to at least 5x and at least twice in snow & less than fair conditions)
On a miserable, I'd still go but places like Field, Willard, Tom & Waumbek would be more likely options. (6 or so miles RT or less again, places I've been too several times. Like I said, I disliek the rain/snow cancels message - it should alter the trip though)
My camping skills are next to nil so that weather forecast would have kept me from this type of trip. Personally, based on my experience & my comfort level while I know that area a little bit, I don't know it as well as others. The idea a fairly big snowfall was happening & navigation was going to be iffy & slow - at least following a broken out trail - I'd have looked at something else.
If I'd had been on these trail 10X & was a veteran winter camper, I'd had probably been right next to him.