My 10-plus-year-old iPod is rock solid technology, hardware and software, just keeps on working. At this point it feels like some retro SF alternate vision of the future we could have had, with simple easy to use things that never broke.
I also replaced the rear panel since I didn't need the beefy 80gb version, and also the lock / headphone jack so they were both solid black.
Rockbox is excellent because it runs off of a basic folder structure, but also has a library option.
You can do the iFlash mod and still use iTunes / the original OS if you like, but Rockbox has proven to be superior in all ways.
If you're on a Mac, be sure to format the main card with a Windows box so its Fat32.
I've been trying to break free from iTunes with a modded 5.5 gen, but Rockbox caused endless errors where non-corrupted songs would skip constantly(1). Wiped back to the default Apple firmware, and voila, no skipping. I tried an iPod plugin for Musicbee, and it appeared to work (files were syncing in Musicbee) but the songs and playlists didn't appear on the iPod. So back to iTunes sadly. I'd love to kick it to the curb.
When you add songs, do it from the original firmware. With the iFlash and all that, transferring files while loaded into Rockbox will cause the issue you mentioned... a lesson I learned after transferring about 80gb of FLACs.
When you boot the iPod, lock it right away and it'll boot to the normal firmware. The transfer speeds are better than using disk mode.
I'm using the original firmware with a while now, it's less error prone and the UI on rockbox isn't exatly polished.
Rockbox is one of those things that is perfect once you live with it for a while. I've been using it since the iPod Video came out (and on a few devices.) The main thing with Rockbox and the modded iPods (iFlash etc) is limiting the EQ bands and other DSP settings. The Sandisk Clip+ is an unexpectedly killer device for Rockbox -- but like anything, the UI takes some getting used to.
Considering they're working around clickwheels with a center button, d-pads with menu button, some with power buttons, others without... its a bit of a marvel that everything is accessible on the devices that are able to be used -- but like I said, I've been using it for ages and can get around some of the odd navigational quirks.
One of the biggest benefits of Rockbox over the iPod firmware is 'timestretch' / playback speeds for files (podcasts, audiobooks.) Its still my favorite audiobook player.
It's a shame what's become of iTunes though...just an awful app.
https://arstechnica.com/gadgets/2019/05/remember-the-ipod-ap...
The reason I am asking is because I am surprised yours has lasted so long. I had two and they broke within two years due to the mechanical hdd inside. (the headphones also broke, within a month each time; really put me off buying Apple products again)