I got a 4th gen monochrome classic, recently. I want to like it so bad, but it's been a major hassle to use thus far.
First off, figuring out how to charge it took ages. I thought it was broken at first. A 30 pin cable didn't charge it from my computer, nor any of the bricks I normally use, nor a fast charging brick with a USB C to A adapter. I ended up finding an ancient iPhone charging brick that worked, thankfully, but it's the only one I have that will charge it.
Second, music. When I got this iPod, it had a bad drive, so I replaced it with a drive from a donor classic (that one had a bad battery, and it wouldn't charge, so I thought I'd messed up. I threw away the iPod except for the drive. It wasn't til recently that I understood that it wasn't charging because of the brick stipulation. I did a lot of research into why it wouldn't charge, but the only thing that people seemed to say was that the board was toast, or that the replacement battery itself was bad, but I tested it with a multimeter and it seemed fine. So I threw that iPod away for nothing). There were a bunch of songs on it (that I didn't like), but a number of them seemed corrupted or something? There were parts of some songs that would skip and get all messed up, but somehow it was accounted for in the song's runtime, which I thought was strange. So I reset the iPod, and had to plug it into a wall outlet for it to finish resetting. Looking into this is the only reason I learned about the charging brick thing, as it was mentioned in passing on one of these posts.
Third, syncing. I have 3 of my own songs on it right now. Why not more? Because it won't sync! It takes 15-20 minutes *per song* to sync. It usually overheats and disconnects itself at some point, resetting all progress. My computer says, "There's something wrong with the drive," but when I repair it, it says there's no errors. I pointed a fan at it to prevent it from overheating, and that helped, but after 10 songs, it disconnected anyway. I think the battery died on it. Windows gave the same error of something being wrong with the drive, but when I unplugged it, the battery was almost drained. It had been stuck on one song for half an hour before that happened though, so maybe not.
Is this just me not knowing how to use it? Is my iPod toast? Do I have to get iFlash or whatever? It'd be kind of annoying to have to spend more on a mod for it than I spent on the iPod itself. By the time I buy one of those, this thing will have cost more than purchasing a used, newer gen classic that doesn't have issues. I'm getting really tired of this thing.