Hi Chris, I was looking at some Allen family to match to my Withers family in Stafford, VA and I saw your post.I read through most of it, and I'm not at all an Allen researcher, but I'd like to make a point or two that may help.
In the 5 years that I've been looking at the Northern Neck land grants in the Virginia Archives, I've noticed two things.The records are sometimes a few years off in Northumberland, even being up to five years late for the granting of land.I think this may be due to the problems between VA and MD and their dispute with Kent Island. Some harsh consequences came from choosing sides with Claiborne.Many of these families moved to Northumberland around 1645 and the first found record books for this area begin around 1649.So, my Keene family left MD to live across the bay, around 1645, and their land grant was given 1652/3, 7 years later.
When I started comparing the records to known history, I saw mention in some records, that the transports were from Maryland across the river to Virginia, that is why some are repeated once or twice, for each time they returned.It is true, there was some fraud, but most listings match up to family ties and neighbors.These transports usually have about 10 folks, but some are for transport of two people, and some for 60, depending on their vessel.Some people are definitely into the transport business and have thousands of acres.Many of these Northumberland men had established properties in MD, and are mentioned in the MD Archive records from 1630s on till they settled in VA.
You should consider your Allen family again, looking at the changes in boundary for counties.I'm pretty sure that Northumberland was formed in 1645.It was split into the middle area of Northumberland, the bottom South to Lancaster in 1651 and the top North to Westmoreland in 1653.Then portions of upper Westmoreland became Stafford in 1664. http://lewis187.home.mchsi.com/History/VA-counties.htmhttp://lewis187.home.mchsi.com/History/VA-counties.htm
I know that my Keene family is in MD in 1635 records, then Northumberland in 1650 records, then Westmoreland 1675 records, then Stafford 1700 records with many of the same families as neighbors.Amongst my Keene/Withers relatives are marriages with the Allens of Stafford in the 1740s.My notes mention that William Allen lived next door to Martha Garner, a sure connection to Keenes of Northumberland. Hope this helps.Cynthia Couch Rodriguez