It's true that wind has a LOT to do with it. So I would inflict some wind on yourself whenever you get a chance, just to mentally prepare for it.

I swear that my first TOSRV (flat and easy) was WAY harder than my first (and so far only) Columbus Fall Challenge (insanely hilly), and 90% of the reason was the wind. Wind is something that can happen on any ride, so you need to be mentally prepared for it, because (for me) it can really beat me down mentally.

As far as the distance, my longest ride before CFC last year (118 Saturday) was I think 105, maybe a couple of miles less (but I'd done several at that distance and difficulty in the weeks leading up to it). I also hadn't done back-to-back centuries all year. I was just short of 50 at the time and it wasn't the slightest problem. But then, we didn't have wind.