i've been thinking about trying to climb some of these in winter myself at some point. i have not heard of anyone doing them all in a single back pack style traverse in the winter. i know people will often combine them in various ways. sugarloaf, spaulding, abraham via ski trails to the a.t. seems to be popular. bigelows via firewardens trail. redington via caribou valley rd. i've heard of the crockers done via the a.t. from both directions. saddleback and the horn seem to most often be hiked via saddleback ski trails to the a.t., but i have seen some use the a.t. all the way.
the main impression i've gotten about hiking these peaks in winter is that the snow depth can make things really difficult. groups of strong hikers have had posted some pretty epic reports about some of these hikes that time of year. i'd say that will be your biggest variable whatever way to decide to hike these peaks.
i'm sure there are people who provide shuttle service to the area, but have no specific suggestions off the top of my head. hopefully someone can speak to that for you. maybe try getting in touch with the "maine road house". they could probably give you some numbers.
take it easy.
bryan