It sounds like you have a lot of information there!
I'm not sure if any of these link to the Margaret Drake in my tree who married Thomas A. Lester.
After I posted this question I decided to get an Ancestry account. That's really helped me a lot. It does so much work for you.
Anyway, according to six other family trees, and I'm not sure where their records came from,
Margaret Peggy Drake, born 1806 in Virginia
married Thomas A. Lester on 24 Dec 1832 in Tazewell, Tazewell, Virginia
Died 8 Jan 1890 in Paint Lick, Tazewell, Virginia
Thomas A. Lester (husband) born 1803 in Tazewell, Tazewell, Virginia
Died 10 Feb 1876 in Paint Lick, Tazewell, Virginia
Parents of Margaret:
John Drake born 1775 in Montgomery, Virginia
married Martha Lester on 12 Feb 1793 in New River, Montgomery, Virginia
Died 23 May 1820 in Laurel Creek, Tazewell, Virginia
Martha Lester (unrelated to Thomas so far in my tree) born 28 May 1777 in Montgomery, Virginia
Died 3 Nov 1859 in Probate, Tazewell, Virginia
Parents of John:
Joseph Drake born 1734 in Augusta, Virginia
Died Aug 1778 in Boonesborough, Kentucky, USA
Colonel in Revolutionary War
Margaret Buchanan born 28 Dec 1755 in Augusta, Virginia
Died 8 Mar 1827 in Franklin, Tennessee
Parents of Joseph:
Samuel Drake and Mary Cox
(I have their birth and death information but it's getting really tedious to post all that)
Parents of Samuel: John Drake and Margaret Weldon
(same, have it, didn't post it)
Parents of John: Frances Henry Drake (born in England, 1701-1794) and Mary Buckingham...Maybe the Frances Henry Drake is the "Sir Francis" my great-aunt was thinking of.
But these records are flawed: John Drake and Margaret Weldon were reportedly born in the 1690's, and Frances Henry Drake and Mary Buckingham in the 1710's...which doesn't fit.
In all my searching I did not find a Francis that could be Margaret's great-uncle.
But, if any other Drakes have information relating to the people I have mentioned, I would greatly appreciate it!
Even though I'm not directly related (Thomas A. Lester had a brother named Isaac Lester who is my direct ancestor, a great times some number grandfather), this is still an interesting part of the tree to me.