Hmmm. I think a Garmin Montana meets most of the requirements of the OP. It meets some of the really important ones like sunlight readability and weather resistance. It isn't cheap though...

It doesn't. Trust me, I know what versions of software I have and have tried. I'd prefer to stick with manual uploads than to rev the OS on antiquated hardware. (And I'd rather spend my spare $$ on bike parts than a new laptop when the one I have does all I need and most of what I want.)