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There's a good book called "How the West Was Lost" that tracks how Kentucky went from a "good poor man's country" into another place where wealthy large landholders dominated--"From Daniel Boone to Henry Clay" as the subtitle puts it. There's an illustration in there of the multiple overlapping claims in one court case that's just amazing.

The same problem is also why Abraham Lincoln's father left Kentucky. He bought a piece of land, but it turned out the man he brought it from hadn't paid the guy HE got it from. More court battles that dragged on for years, ending with the Lincolns evicted.

It reminds me of the Mark Twain line about the town that had one lawyer and he was starving. Then another lawyer moved to town and now they're both rich.