@Jason Samson
So, in mid-late 1600s many indentured servants didn't get land when they finished their indenture. They just moved up to the frontier and 'squatted'.
My question is: what happened to them eventually? Did they ever acquire the rights to the land they tilled? If so, how? If not, where did they end up?
All you have to do is look at my state and what people are called here - Sooners. That came from when it was decided to open the state up to people, and some people crossed the line ahead of, or 'sooner' than legal.
From your story perspective, you're dealing with people that moved to the frontier into what was considered unclaimed territory. If the land they squatted on wasn't claimed by anyone (and sometimes even if it was), then they'd build their cabin / hovel and start farming. The old saying that possession is 9/10ths of the law is relevant here.
That's how a LOT of small towns in America got started. It'd go from Frank's land to Franklin, Brooks Town to Brookston, etc. While the land at that time was all claimed by the Crown (you're in pre-Revolutionary war times), realistically so long as the new settlers continued to plead fealty to the Crown, they were left alone.
And if they weren't, then they either moved further west or moved six feet down.