I guess the only reason I would take sleeping gear would be if I thought that with the wind in particular I was going to fall far enough behind that I would miss a night. But over 3 weeks with bookings every step of the way, you pretty much need to be able to keep up, so how tough are the days.

In your situation I would probably not take a full set of camping gear, I would take survival/ultralite level stuff like a tarp or bivy. I would not be taking all the cooking stuff etc... unless you are taking that for some other reason. So overall your ability to survive hurricane winds and rain, or just a night out, might only cost a pound or so.