I have struggled so much with this, and could write pages. I have just plain accepted that my love of having my entire music collection accessible to me at all times, in all situations, is no longer going to happen. I had a 128 gb iPod classic that was expanded to 256 gigs. That fits everything. It died. I bought another. It died.
Everywhere I looked, either the other options were way overpriced, or didn't give me options I wanted in my vehicle (like having the cover art come up on the stereo). Everyone was streaming everything, and everyone seems to use their phone.
I just said fuck it and got the biggest iPod Touch I could find, and now use that. I am an Android user, but my music collection (while it IS encoded to mp3 at 256 VBR) is run through iTunes. So I debated getting the latest iPhone at the most memory available. But with all the extra stuff on the iPhone, I still figured I'd probably not be able to get everything on there (my music collection is just under 204 gbs), so I just decided not to, and have stuck with the iPod Touch I have, and I go in periodically and switch out albums.
I carry my laptop, so I have access to my entire collection at the office, but in going mobile, I'm stuck with the iPod Touch.
I know guys like myself who are big time audio geeks are not the crowd Apple is eyeing, but I still think they really missed the boat by not having a huge capacity iPod still in production. Something 256gb or more. Even if it was priced at $500, I'd buy it in a heartbeat.