Selma has given some excellent tips, and is a Virginia researcher.

I have one thing to add (as a non-VA researcher):
Since you have done quite a bit of research from 1790 forward, you have probably already come across these resources. Still worth a mention here.

1. Re-check existing records
a) at the LVA:
Burned County Notes: http://tinyurl.com/9horm5

b) Lipscomb family vitals.
It is important to know Henry's 'fit' in the Lipscomb family genealogy AND associated (collateral) surnames.
Was Henry's father named John?
He died between 1775-1779. His wife survived him.
Mrs. John Lipscomb appears to have inherited from her father (a Madison).
Could her son, Henry, have inherited from his Madison grandparents?
(More surnames and possibilities.)
________________________________________
Lipscomb Genealogy:
Click on the pages to view from the left navigation pane. (John, p. 423)