Ol' (mostly) reliable
I've had a long history with digitally compressed music; I can remember encoding CDs on a P100 machine, and friends who had RAM-based MP3 players; if the battery died, then you lost your music!
However, back in the day I mostly stuck with Sony's minidisk players; the later models gave you up to 320 minutes per disk (at around a quid per disk), Sony grudgingly let you digitally copy music over to the later models via USB, via the abomination called Sonic Soundstage, and you could get over 50 hours playback from a single AA battery.
And the MP3 players at the time frankly couldn't hold a candle to either the battery life or song-storage capacity, especially since I could easily carry a half-dozen minidisks with me!
Still, once solid-state capacities started to grow past 1GB, I did start using MP3 players.
I can't remember exactly when I fell into the Apple eco-system, but for me, the iPod peaked with the 3rd gen iPod Nano. The "shortened credit card" form factor was far easier to keep in a shirt than the tall/thin form factor favored for the other Nano variants, and 8GB gave the Gods of Random (tm) a fair amount of stuff to play with.
Plus, at that point, iTunes was measurably better than Sonic Soundstage.
I did eventually drift away from iPods, but ended up being roped back in entirely by accident; my old MP3 player died, the day before I was due to go on a 20-hour coach trip to Germany, so I nipped into a local Cash Converters and grabbed a used 120GB iPod Classic.
And that thing lasted for over a decade; it was a bit dented and scratched when I finally parted with it, but functionally, the only real issue with it was a diminished battery life. And even then, I think I still got about 50 quid for it, via Ebay...
Alas, things haven't been quite as smooth sailing since then. I did pick up a "refurbished" iPod Classic with a 128gb SD card, but it was prone to locking up. I suspect the battery wasn't quite up to snuff, as it was generally fine when charging/playing via a dock.
I also dabbled with iPod Touches, but all the ones I bought experienced the same issue; after a while, the headphone jack-port would fail. I did try to get a couple of them repaired, but this was never successful.
In the end, I bit the bullet and upgraded... to a 128gb 1st-gen iPhone SE, from CEX. Since it was both cheaper than an iPod Touch and is the last iPhone model to have a headphone port.
And I'm still using said beast daily, while sat at my work desk.
Smeg knows what I'll do when that finally dies (and/or I can't source a good replacement from Ebay or similar).
For all that iTunes is a bit pants, it's still better than most options, especially since I'd have to deal with the joys of exporting all the stuff I've set up; I carry around 10,000 songs with me, split across 50+ playlists, even if I do usually just let the Gods of Random pick the songs for me ;)
I have dabbled with porting stuff over to Android - e.g. via iSyncr, which uses AppleScript (or somesuch) to query iTunes and then transfers the given playlists and songs to your Android device - but it's an extremely clunky process and Android is fundamentally a far poorer host for locally stored music, especially with the number of tunes I carry around.
And as far as I know, there isn't any Android player which lets you tag/rate songs, which still remains my favorite way to process new tunes: stick 'em in a playlist, sync to the player, and then mark them as 1-star if they're crap.
So, yeah. I've had a good run with the classic iPods, if not so much the more modern iPod Touches. It's been one of the few places where Apple's It Just Works ethos properly clicked with me!