Vann - am posting here, but you are welcome to email me, as we may get more into this than is of interest to everyone else.
I am told, but have not confirmed, that UVa's Special Collections Department may have some info that we'd be interested in.
Supposedly they at least have a whole section (maybe not in special collections) on early Caroline/Rappahannock records, which is where we'd have to find anything that exists. I think I saw somewhere that the earliest stuff is under "Sitenborne (not Sittingbourne)Parish" - of course, you probably already know that it was in Old Rappahannock County. When Old Rappahannock Co (established in 1656) was abolished in 1692, the parish north of the river was in Lancaster Co., and the section south was in Essex Co. St. Anne's Parish was created from the Essex Co. portion of Sittingbourne Parish, but that wasn't until 1704.
Caroline was created in 1728 from Essex County and that is where we find Charles in 1737 and David by 1779. A couple of serious VA geneologists tell me there is little chance of success in researching these early counties of Old Rappahannock. Caroline records are even more rare. Apparently, almost all of the colonial wills, deeds, and marriage records are gone. The few land and other transactions available would be in survey books, chancery court suits and deeds and it might help to look in counties other than Caroline, because the others would describe transactions which affected Caroline citizens. One lagniappe in researching Caroline is that its Court Orders were preserved from the year 1732 - so I guess we might get lucky.
There are also some early broadside/newspaper collections from that time and that area - I don't know if they're on film or available to anybody, or what. Complicating the search even more is the fact that since Caroline was not made up from a single county, (territory from Essex, King and Queen, and King William contributed toward the formation of Caroline in 1728,) records are mixed and only Essex County has fairly complete early records. Would it be worth looking there? I don't really know.
UVa has local court records on microfilm for Old Rappahannock - Caroline wills have actually been destroyed, but the indices still exist, so you can search those, I'm told, for names. We won't get anything from the marriage bonds, because those begin in 1795.
The west reading room at UVa holds the microfilm stuff on census and historical Virginia and I'm told they'll help if you show up in person. The Archives and Map Research room will have Bible records and genealogical notes people have contributed.
The Land Office Grants index cards are online- they show nothing for a Traynham, and I can't imagine why a Rev. War soldier would not apply for those grants, if only to sell them..it's that alone that makes me wonder if David was a Loyalist.
By 1785, the whole family, minus Benj. move to Halifax and were only there 7 years..
Herein endeth the entire knowledge I have of what may or may not be at Charlottesville!
Don't know if that helped or not, but let me know what you're thinking.
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