Probably not. It's not hard to notice that while volatiles may flow from the hot side to the cold side, it's generally a one-way trip. Most attempts to model such a planet as habitable even on the thin strip involve trying to hypothesize some way that the volatiles could end up circulating rather than simply making the one-way migration, but personally I'm yet to hear a convincing way that could happen. And that's for the lower bar of "is life possible at all", not the much higher bar of "could we be happy living there".

YMMV, since it's all opinion and conjecture right now.

But in general I wouldn't expect much wind. The hot side is in vacuum because the only volatiles there are the ones just baked out of the fried ground or perhaps some volcanic activity, and the cold side is in vacuum because everything's frozen, and if there is some tiny pressure gradient you'd never notice the resulting "wind" as the vacuum flows past you, probably at rates roughly comparable to what the ISS experiences as "wind" in its low Earth orbit.