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I installed Rockbox on a 5th Gen iPod a few days ago, and I've been living with it as my player of choice ever since. It's an interesting piece of software, with a few hidden caveats.
First (I need to get this out of the way) wow! Aesthetically, Rockbox is a throw back. And not in a good way! In a, "probably looked bad in 2005" way. I know I shouldn't care, but, well, I do. I keep stepping through themes and I'm basically at the point of trying to find the one with the least amount on screen. Ugh. Soooo close to doing my own, it's not even funny...
But!
If I hold my nose to get past the aesthetics then it's a really capable firmware replacement, just maybe not laid out in the best possible way. It's configurable, the database works well enough, and it's played everything I've thrown at it-ish (see below), which is the most important thing.
But! (Again)
It's also had some problems.
The iPod takes an age to appear in explorer when attached via cable. Like, minutes in the worst case. It only seems to reliably connect over USB3. When attached to USB2 it'll disappear, randomly. (It's definitely not powering down. I've been in device manager to prevent that) And, worst of all, I found that the vast majority of the flac files I'd copied over wouldn't play to the end. They'd jump, as if corrupt. (Turns out that they were...)
It took me several days to work out what was going on, but eventually I stumbled on some old forum posts. It seems all my problems are related, and all of them are down to "You shouldn't copy files to the iPod while Rockbox is running". This seems a little odd to me, but I can confirm, it is the fix. Once I reboot to Apple's firmware -- oh yeah, Rockbox dual boots! That's quite the thing -- I could copy several gigs of flac files over, reboot back into Rockbox, and they all played perfectly!
I would have preferred not to have to reboot for this, but it's not the most onerous thing in the world, and to be honest, so far, the ritual of plopping files onto it for the day ahead has been an enjoyable one. It's become part of my morning routine!
I'm enjoying iPod life...