Interesting idea, though I suspect the more regular version in the final diagram could be made to work reasonably well, with less work on the planning and surveying sides. Each block would have a different shape from all its neighbors, so with trees, differing houses, etc., you'd have much of the same benefits.
That said, I don't see that this would have any impact on HOAs. More significantly, I've seen developments with straight grid layouts that are closed, only having one outlet to a public road. That could happen just as easily with a wavy or liquid grid.
That said, I don't see that this would have any impact on HOAs. More significantly, I've seen developments with straight grid layouts that are closed, only having one outlet to a public road. That could happen just as easily with a wavy or liquid grid.