What's the best music player software that will cooperate easily with my iPod Classic...

didnt foo_dop have limited compatibility?

I use copytrans and mediamonkey.

Correct. There's some compatibility limitations with iPod Shuffles and iOs based device support only goes up to 4th gen for iPod Touches and iPhones.
For the 'regular' iPod models, the only thing not supported is the Genius feature on the later models (do people even use that anyway?).
wiki.yuo.be/dop:start

I've never had a single issue managing my 160GB Classic with foo_dop.

Ever had any issues with Copytrans? I used Copytrans for several years and quite liked it. The UI and how you could keep the program on the iPod itself. But then it started acting weird and I had to switch to Foobar + foo_dop. I still have no idea what it was about..
File transfers started giving out errors and not moving over tracks seemingly at random, making it necessary to transfer files in small bunches of couple dozen at a time, remember the amounts of errors it gave, and if it did, to check which tracks didn't get transferred and redo those (as 1 error equalled 1 track not transferred). I tried reinstalling and updating Copytrans, finally resetting iPod to factory configuration with iTunes. No luck, still the same. I contacted Copytrans tech support. They were puzzled as well, eventually suggesting the possibility of the iPod's HDD being quite far on the way to shitting itself. I ran the iPod's own disk diagnostics as well an HDD scan on the computer. Both came out 100% OK. Copytrans kept on acting odd. Shit's weird. I gave up on it and tried out Foobar2000 + foo_dop. Never had one single thing fail with that yet.

Unironically this, I fucking love Clementine

I hate myself for saying this, but rsync + Rockbox is a fucking cozy time.

Install rockbox desu, you can then transfer music via USB mass storage

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I use MusicBee with mine. It werks just fine

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Slight unrelated question: If I use rockbox on my ipod classic, can I format it in NTFS?
Back in the day I also used my ipod as a convenient portable storage on trips, but it started to lose in convenience because it was formatted in FAT32 and I had to store increasingly larger files as time went on.

Rockbox on the ipod. Then anything Will do the job

>Features we will not implement
>Support other filesystems than FAT (like NTFS, HFS or ext2/3/4)!
>>Adding support for more filesystems will take away valuable RAM for unnecessary features.
>>We will however consider additional file systems when they are required to support a player adequately (e.g. a device whose bootloader cannot use FAT). Support for newer FAT variants (e.g. exFAT) would also be strongly considered as they become more widely used.
rockbox.org/wiki/NoDo

They're really trying to keep RAM usage of the OS low to maximize the amount of data that can be cached from storage.
For similar reasons, many routers don't support NTFS or exFAT despite having enough computing power to run the respective FUSE drivers.

same Well fair enough. Thanks for clearing that out.

bumpan for more suggestions

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just get rockbox you pleb. Also get an iflash SD card board

Rhythmbox is what I use on my iPod. Good for getting music off it, too.