I don't know anything about the Daviess Co., Mo. Woodersons but I may be able to help you sort out the Richard Woodersons by providing the dates for the Fayette Co., Pa. family.Richard Wooderson, Sr. b. abt. 1785 in PA. married Rebecca Jennings b. 28 Nov. 1782. She died 22 Dec. 1837. She was the daughter of David Jennings b. 1741 in VA. d. 29 Mar 1824 in Fayette Co., PA. and Mary Henthorn b.14 Nov 1739 Codorus, York Co., Pa. They were married in Codorus in 23 Jul 1762 but moved to Fayette Co. soon after.
It is quite possible that Richard remarried since he was still in his fifties when she died, although I have no documentation of any other marriages. They had four children that I am aware of David Jennings Wooderson, William Wooderson, Sarah and Rebecca Wooderson.
I don't have Richards death date but he died in Wayne Co., Sand Creek Twp. Ohio. He may have had a son move to Davies Co. Mo. but my records do not follow the family on down any further. Jennings descendants moved on to Ohio and onto Iowa in 1854