Jamey,
I find a couple of your ancestor names interesting. Some of the various trails I have followed turned up the following names:
From Washington Co., KY Marriages:
Anna O'Bryan m. Charles McLaughlin, 19 Aug 1817
William O'Bryan gave consent.
(Any Relation????)

In some of my other papers, I was sent by another Bryan researcher:
(Possible line: The William Bryan who died in St. Mary's Co. in 1739-the will in the Bryan Book-was s/o Bryan O'Bryan and Katherine___.)
Richard Wimsatt, d. 1725 m. 1694 Katherine, widow of Bryan O'Bryan.. Had children Richard and John Wimsatt.

I know what you mean about the French Line. My ggg-grandmother on another side of my family was Eleanor French Brewer Cole, sis of Susanna French Bryan, both d/o Raphael and Mary French.

I have to wonder if the families were interwoven in Maryland also. Just a thought.

Sheila