After a while you start to accumulate boots. I think I have four pairs of boots & last years trail shoes & this years. The boots I wore the other day are just slightly more flexible than my plastics but do well in mud & slush. I've got enough so I can micromanage which ones I need for November weather or September on rocky terrain or in the woods on dirt. (Somebody had to take Imelda Marcos place!
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As far as summer goes, I've given up keeping my feet dry on wet hikes, if they dry out quickly ater oing through the brook I'm happy. (the summer shoes fit well so I don't get blisters when they are wet.)
If you are going to need crampons or the snowshoes are going to used on steep terrain, (up East Osceola for example) stiff boots (either plastics or heavy leater crampon compatiable boots are the way to go)
A weekend camping in the Pemi & staying low is ideal for Sorels. Sure some people have stood on Washington withSorels & some have camped in the Pemi in plastics.
Gear has changed, Katoola (spelling is likely off) makes a type of crampon that you could just about put on sneakers. They aren't up for vertical ice but they would handle almost all regular hikes up the 4,000 footers. Companies (TNF, Columbia, Merrell also make soft insulated winter shoes great for snowshoe use)
If you hike with the same AMC group after a while, they will get to know you & your ability to hike & to stay warm. Some of the leaders are now wearing the alternative boots. If they don't know you, they would much rather be safe than sorry.