I found your approach to visiting Accomack for a genealogy investigation trip very interesting. The idea has crossed my mind and I also thought about doing it in September or May.
I am primarily a Bennett researcher. I too have many bits and pieces that still require more verification. My William Bennett, Sr 1710-1783 or 1788 and William Bennett, Jr 1739-1802 both served in the Revolution. Senior was in the Army and Junior was in the Navy as a Master Mariner.
I suspect our immigrant ancestor was the Samuel Bennett who was claimed as a headright on Pimino Creek by John Stringer in 1669 along with a William Willet.
I suspect that Samuel Bennett b.c 1802, orphan of William Bennett Sr didn't travel to Clinton Ohio alone. He was married in Clinton in 1824 and I suspect he made the journey in 1823.