My son in law has one I'm 5' 8" 215 lb it has more stretch out room than I could ever use, he an inch taller than me. He rode it to Deals Gap a couple of years ago no problem other than 125 mile tank range. Spoke with a guy riding one last summer he was at least 6' 3" he said it was comfortable for him, and he didnt look cramped up on it.
No problem with 300 - 400 miles a day on my Gen1, I dont load too heavy Hi mount exaust cancels out saddle bags. Tail & tank bag holds enough for a couple days. Rides great on freeway, Zero Gravity DB windshield is much better than stock I'm 5'9" wind hits me at chin.
Fall would be good, I agree that riders will more on the chill by then. More time to plan and organize. Plus park bikes in their group on arrival would end a lot of confusion and save time. All I need now is a hot tub full of sweaty drunks and I'm set.
We stayed at Iron Horse 4 years ago, no food, no beer, bunch of douchey wanna be pretend hard ass Harley clowns. Screw that, my crew is in for Fontana.