I don't think I could do the whole thing.
I'm getting close to being forced to get a new job (Long Story), and probably won't have much leave.
I could do part of it.
I'm sure if you post your plans, you'll get several people that'll join up for at least part of it.
I would think it might get a bit complicated and lose some of the luster trying to organize a big deal (Just my opinion.. Don't like big crowds, Don't like riding in large groups)
BTW, after Tulsa Oklahoma, you'll be looking for some twisties, and they probably won't be along 66. Might want to plan quick detour every once in awhile, or make sure that you really want "the experience" before setting out.
Also, most of original Route 66 roads are in pretty bad shape. Here in Oklahoma, I think we have some of the better, longer stretches, just not too many curves in them. Lots of nice small, old, towns to go through.
I think the trip would be a blast !!
2008 BMW R1200RT 7200 miles
2005 BMW R1200GS 13000 miles (Sold)
2002 Yamaha FZ1 (Sold) 11000 miles
2002 BMW K1200LTC 29900 miles (Sold)
2002 Yamaha VSTAR-650 Silverado (Sold) 9100 miles