Great List. Nos. 7, 12 and 13 have pretty much been taken care of. With the last software update, adaptive brightness works. I have the new Classic 3G for the very reasons you mentioned, and love it. And with the Classic or the band adapter for the Sport, pretty much any band is now available.
Also, as to number 6, the Standalone Gear Navigator app integrates with Google maps/traffic and search data, giving you walking, driving and biking route options. Worked great on the original Gear S after memory management update. It uses much less battery on the Gear S2 than the Gear S, which is even better, but I have had some trouble with it crashing on my Verizon Gear S2 3g. But it seems like most folks don't have stability problems and the developer generates updates regularly and responds to inquiries quickly. For $2.99, it is totally worth having a standalone Nav app.
I hope for the others you list, especially a larger screen male version, and more apps, especially other standalone streaming music support. Milk is great, but Spotify would be better.