And I'd pay good money for a more complex iPod Classic. I need its space but the software is simple in ways that regularly annoys me; I believe there's significant room for improvement.
Agreed. In this sense I'm worried that google will lean more toward "Internet For Dummies"(e.g. losing the + feature in favor of double quotes to make way for G+), attempting to coral my internet use into certain patters the same way Apple seems to (like removing the "Reader" link from the google bar to showcase G+).
Look into rockbox (rockbox.org). Its an opensource replacement firmware. I take listening to my music seriously enough that I need a dedicated device with good software. Since I found rockbox I haven't bought a mp3 player unless they were already on the supported hardware list.
The rockbox UI structure can be a bit cumbersome to learn because there is a lot of functionality there, but I've never found anything else that comes close.
Sadly it seems the iPod Classic isn't supported... Oh well.
Honestly, if no-one beats me to it, one day I'll write my own Android music player that works the way I want. The spec's been solid in my head for years, it's just that's the first platform I've had which would make that a practical possibility. With falling smartphone and memory card prices and improving battery life, the days of the standalone MP3 player are severely numbered.