Thanks all. Here are my thoughts after your suggestions.
I think I'd rather just keep moving too, except since I am a retired minister and seminary lecturer, I do have an interest in visiting different church traditions in different parts of the country. I think I would enjoy it and as a perk I just might get myself invited to a few Sunday lunches. I certainly won't be wearing my Sunday best clothes tho
I do like the idea of using a warm-shower host to keep the bike and take a bus etc to my reunion IF it looks like I will be delayed. That may take the pressure off and if delayed at all I can just enjoy my ride without worry.
Jamawani, it was funny you put down an example date of May 20. I had made a tentative date on my first attempt at guessing a departure and I came up with May 21 to fly out. I like the idea of perhaps arriving earlier in the week so maybe the 18th would add a couple buffer days and I could arrive on Wed rather than Sat.
I also just discovered Skiplagged.com that will let me see a timeline of prices so I can see at a glance which day of the week and which airline has the best price. Just now looking I see that flying into Washington DC instead of Richmond or Newport News is $100 cheaper. It surprised me that Richmond and Newport News were almost the same price.