One thing I'd really like to see would be an "Advanced" mode. The iPod as it is, is very user friendly and doesn't present any complicatedness that would cause confusion in someone illiterate. However, I would like a little of that complicatedness. Most specifically I'd like to be able to view statistics of files saved on the iPod. Things like format, bit rate, maybe where you got it from (downloaded on iTunes, from a CD, etc), resolution (in the case of videos and photos) and things of that nature.
I'd also like them to bring back fullscreen album art. Well it wasn't really full screen, but anyone who's used an iPod Video will probably know that among the various functions you can perform when you click the middle button on Now Playing, one of them simply enlarged the album art and made it mostly fit the screen. I thought that was neat, and now they've gotten rid of it.
Another improvement that could be made would be to be able to turn Repeat on or off without going into Settings. It's nice that you can toggle Shuffle from the now playing screen, but I don't know why they left Repeat out of it.
Oh, and DRM kinda sucks. It only happens on iTunes downloads of course, but it's annoying when you want to do something with your downloaded songs. However, Apple has started to do something about it, it's called "iTunes Plus." Basically an iTunes Plus song has double the bit rate of a regular song (256 instead of 128) and no DRM, so you're free to burn it, distribute it, or use it however you want. They also cost the same as a non-Plus song, so everything about it is great. The only thing is, not all their songs are iTunes Plus.
Firewire would be nice too. They slowly started taking away Firewire support a while ago (now you can't even charge with it) and I think that sucks. Firewire is fast. Even though USB has a higher mbps, it can't stay at that mbps most of the time so instead of 480mbps, USB gives you maybe 300 or 200. Firewire stays at a constant 400 (or 800) so it's nice and fast. It's no big deal if you're only syncing over an album or a song, but for big syncs like video and such, Firewire would be nice. And I'm sure that iPhone users and their 2+ hour syncs would also appreciate it.
Anyone who knows iPod history will understand this, we really need more stuff in the box. There was once a time when you got a dock, a remote (it clipped to your shirt and you could control your iPod with it), a case, their awful shitty headphones, and I think an external charger. That was what came with your iPod. And in the day of Firewire you also got both a USB and a Firewire cable. Now you get their awful shitty headphones, a dock insert for your iPod radio, and a USB cord. If the iPod wasn't such a nice player I wouldn't have gotten one for the total lack of stuff in the box.
Bring back the bigger engraved text. On the older iPods (video and before) when you got text engraved it was nice and big. On the Classic it's pretty tiny, and you still have the same size limitations as when it was bigger.
Make the click wheel more responsive. It used to be that you could touch it anywhere and you'd get a response, but on every Classic I've used it's been totally dead in the center and would randomly have other dead spots on and off. Annoying.
Fill the interface with PG-13 content so parents will stop buying them for their spoiled asshole children. I'm being serious.
Give it a radio to shut up the "it doesn't have radio" people. It's not like they'd even listen to it though, since listening to radio somewhat defeats the purpose of the iPod. Then again, those people usually have something against the iPod anyway, so they'd just find something else to not like about it. Maybe we don't need a radio after all.
Those would make the iPod better. Get crackin', Apple.