I'm with you, PoorinRichfield! I salute your effort to find a product that makes sense!
I agree that looks and quality matter, but yet so few lights pay either any attention. It's particularly galling when you consider that basic (or even exact, I'm sure) chintzy, inconvenient, black plastic articulated seat post clamp you pictured is the same thing that has been in use since at least the '80s. Almost no one has bothered to even consider a better way. WTF?
Anyway, my go to taillight these days is the Knog Road R. It's not super chic looking, but it looks pretty good, is easy to use, performs very well-- excellently, even-- and is super sano to mount.
Oh, and thanks for the heel light heads-up. Interesting...