Migration from Montgomery County, Virginia to Warren County, Kentucky

A message came across the Virginia Montgomery County message board this summer that inferred connections between families found in Montgomery County, Virginia in 1796 and families then found in Warren County, Kentucky.  I am going to copy the entire query because there are several thoughts in the below that I want to look at eventually.  My Ichabod/Bird Hensley is found in Clay County, Illinois in 1829 in a marriage record.  The bride in this record is Nancy Webb.  I suspect (but have not done the proof process) that Nancy's family had lived in Warren County, Kentucky before their move to Illinois.  And I know from many years of research that there were Webbs in Montgomery County, Virginia.  So I am interested in specifically looking at the families who moved together to Warren County, Kentucky from Montgomery County, Virginia

Here is the Query from the message board:

Jacob Smith next to William Stapleton put his land in the hands of Attorney Hugh Crockett in 1795 and moved to Warren County KY.  This land was later sold to Jesse Hall through Attorney Hugh Crocket.  This Jacob Smith had a wife named Elizabeth this is per the deed.  This Jacob was one of the two Jacobs on the south fork of the roanoke. This Jacob is the one that was next to John Picklesimer and William Stapleton.

Jacob SMITH's land was next to the Widow SHILLING, WEBB and LEWIS

This Jacob Smith disappears from the Montgomery County tax list in 1796.  He is obviously the Jacob surveying land in July 1796 in what was to become Warren County.

This Jacob Smith died in 1810 in Warren County KY his wife Elizabeth died in 1814  Her will listed children...  one in particular was Mary Smith that married Mark Lykens.    Mark Lykens too went to Warren County KY.  And the court record for his marriage to Mary does say Mary's dad is Jacob.

The sons listed in Elizabeths will were Jacob, David, John, Rowland

In July 2014, I am spending some time with my files and piles that are filed in the Webb cubby in my office.  It is NOT looking as if this migration from Montgomery County to Warren County, Ky is going to be fruitful for my own Webb line.  I found a copy of an e-mail that came across the Webb mail list 7Oct 2002 from Mike Webb in Florida.  

He offers information about the Webb family with names of William and John found in Montgomery County, Virginia during the Revolutionary War.  Julius Webb has daughters Kezekiah, Nancy and Millian.  Other names of Webb men are Augustine and James who married Jane Claxton in Botetourt County.  Both Augustine and James moved to Shelby County, Kentucky which is between Frankfort and Louisville rather than the Warren County area according to this e-mail.  These Webbs lived on property near Rockfish Creek in the 1760's in Virginia.