The freestone boots are wonderful for support, and pretty darn rugged. I have no experience with the Chotas, but they are a very respectable company. I personally would wait for the new simms soles to come out (not sure if they are in the catalog or not yet) since they really are awesome. I have semi-flat feet and weak ankles (too many sprains) but I havent had a thing to complain about with my freestone boots yet. Check Sierra trading post too for boots. THere are always some good boots on there for real cheap. And the reviews people post will help out a lot in your decision.