Both Bob and Dave are super nice guys and I'm sure wouldn't mind your picking their brains for insight on routing and other advice.
I've not ridden much in the northern part of the state, but central and south, things don't tend to be too windy in August, generally. If it were me, I'd go with whatever direction is most logistically easy for you. Sounds like you'll have plenty of training in this year so finishing shouldn't be an issue for you. Since you're not racing it, trying to pick up the slight advantage of an afternoon SW wind isn't that big of a deal. Good luck and be sure to post a ride report!