[manomanowicz]

MY recommendation would be a modified iPod 5th or 7th gen Classic if you don't mind the larger size. These iPods can be upgraded with larger batteries and flash storage instead of a hard drive making them long lasting and robust.

You can do the modification yourself on iPod with a broken hard drive or buy one on eBay already modified. (Tip: The 5th gens are easier to modify than the 7th gens since they come apart a lot easier.)

Personally, I use a 5th gen Classic with 32GB of flash and a new battery. I modified it myself with a compact flash card and a new battery. It's been in use for about 3 years and I've had no real issues.

[dalke]

Thanks for the pointers! My backup plan if I can't find something new is to get a used nano. I hadn't considered a Classic.

Alas, I'm in Sweden so eBay + shipping + customs adds a chunk, but maybe I can find someone here who does that.

[jacobush]

How do you copy podcasts and such to these old iPods? iTunes is being deprecated right?

[patrickk]

Foobar2000 with an iPod add-on[1] and a podcast add-on[2]. You don't need iTunes directly, but probably an older version of iTunes in the background for compatibility when syncing. Oldapps.com has you sorted for that.

I personally use a modded 5.5 gen for daily listening, it's vastly superior to using a smartphone. It has a huge memory and unbeatable battery life. With cheap replaceable batteries and SD card boards, it should essentially last for years/decades. The firmware is much simpler than iOS, so it doesn't matter that it's not maintained, it simply works.

EDIT: OP is using a Mac, so I'm not sure if this is feasible. It does work well on Windows though.

[1] https://www.foobar2000.org/components/view/foo_dop

[2] https://www.foobar2000.org/components/view/foo_podcatcher

[andyjohnson0]

Replace the firmware with RockBox and it presents itself as a normal USB storage device. Just drag and drop the files.

[physicsguy]

Syncing music still works fine on Macs/Windows. I'd actually go as far as to say that on Mac it's an improvement, becasue you just have a 'Music' app and a 'Podcast' app, and when you plug in an iPod you can see it in Finder.

[spondyl]

It's perhaps more like elements of it seemed to be integrated into Finder so it'll mount as a device and you'll see the familiar iTunes style sync UI