I mentioned my recent round of Apple support calls on Facebook and added that I was getting disillusioned with Apple support.
To which Ted replied:
Disillusioned? Hah! I've got you beat by several light years!
iTunes running on my Windows 7 machine won't sync music at all with my iPod. I've had the problem since the day I bought the iPod in 2012 and (foolishly) updated iOS from the 4.whatever it shipped with to the then-new 5.0. Ever since then, it sees the entire memory space on the iPod as "other." Deleting everything doesn't help.
I went through three levels of Apple tech support, which offered increasingly ridiculous suggestions, all of which were useless. The third level finally referred the problem to "engineering." They told me the USB controller in my motherboard's Intel chipset has an unspecified compatibility problem, and I should go out and buy an add-on USB card. It turns out that the motherboard already has a second USB controller with a different chipset (intended to provide USB 3.0 support), which is effectively the same thing as buying an add-on card.
As I expected, plugging the iPod into the second controller made no difference. After I reported that to the 3rd-level tech support I had been dealing with, all communication with Apple abruptly ceased. I received no replies to repeated e-mails and voice-mails. My guess is that Apple has a policy that when they can't solve a problem after a certain number of attempts, they put the customer on a blacklist to avoid wasting any more of the shareholders' resources.
It turns out that one of the first-level technicians had the only workable solution: He told me to buy a Macintosh. I copied my iTunes library to a spare Macintosh that belong to my then-roommate. I would then rip CDs from my collection on my computer, copy the files to a flash drive, and SneakerNet them across the room to the Macintosh.
That was only a mild inconvenience until I had to move, soon after which my former roommate sold the spare Macintosh. We moved the iTunes library to his own Macintosh. I still rip CDs and put the files on a flash drive, but I save them all up until I'm ready to drive the 12 miles to my former roommate's new house.
I haven't been able to come up with a better solution than that, other than possibly buying a used Macintosh on e-Bay just to use with iTunes/iPod. The only non-Apple device remotely comparable to the iPod is Samsung's Galaxy Player. It took a lot of effort to find any store in Los Angeles that had one I could look at. When I drove to that store and looked at the Galaxy Player, I almost immediately understood why it was so hard to track one down. It's so inferior to the iPod that there seems little reason for it to even exist. That also may explain how Apple feels they can get away with disposing of "problem" customers by ignoring them.