Agreed. Like waders, you come to the realization that there's no pair that's gonna last more than a few years of heavy wading, and it becomes a replacement item.
In my experience, Chota's last as long as any, and are pretty comfortable for my feet. As I said, I think the Simms are on par, if not a touch above in quality. But it comes down to what kind of feel you like. Chota's are roomy and supple with little support. Simms are stiff and tight with tons of support. How much support you want and need is very much an individual thing. We all have different strides and body shapes.
I can honestly say I have never sprained an ankle in my life. Ankle support isn't high on my list. But, everybody's different.