::UPDATE:: As of 2/10/16 this is still a problem.
Back in December, I got on the phone with one Apple representative who ran into a dead end, and he then made plans to call me back at an agreed upon a time. He never did. This same representative tried to distract me by saying that the "world was changing" and that we're "moving to the cloud"... as though this were my fault for being behind the times.
That's fine and all... But what does that have anything to do with the fact that there is a glitch in their software that negates user custom settings, erasing literally years of fine tuning?
What is iTunes but the promise to have control over your music library? What was it but an music nerd's dream? What is it becoming but a sloppy hybrid of rushed out ideas, grasping at straws to stay "current"? (When other people would ask, "Why do you have a Mac?" I would say, "Because they work. Perfectly. All the time. They're so intuitive. So carefully made. Works of art.")
That's what I used to say...
I called again on my own after deciding no one was going to get back to me. On the second call, the representative told me I'd be called back by a tech representative. They left a voicemail while I was at work that left no direct means of getting back to them. This was also back in December.
I "solved" this problem by re-unchecking the desired songs, painstakingly, one by one—and I'm still frustrated. This took hours of free time over weeks and it never quite got to where I'd had it before. I was basically resigned to letting it go... until...
I went to sync my phone today and I realized that iTunes had rechecked all of my purchased songs again. Great. I've been trying to back up my computer extra frequently in the meantime, and, like others have said, I've been crossing my fingers that I can back up to a "good" version, but what kind of solution is that? Especially if this is a recurring problem...
I'm currently on hold waiting for an apple care representative to (in all likelihood) try to get on my good side by telling me he/she understands my feelings but then offer no objective assessment of the problem nor a course of action to resolve the problem.
::LIVE UPDATE:: I am on the line with an apple representative at 11:05 eastern time (After a 15 minute hold). He is empathizing with me—rephrasing my complaint and emphasizing how frustrating it must be. Asking me details about what others have said on this forum.
He just put me on a hold to reach out to a senior supervisor.
(Does he not have access to the forum? He said he "searched" for others with my issue and "it's not trending". Really? Interesting, considering Exhibit A, this thread exists and is pretty easy to find with Google. Considering Exhibit B, that when I called in (twice) in December, I clearly laid out the issue, and one would hope they filed those away somewhere useful. Considering Exhibit C, When I called, the A.I. sorting mechanism asked me if I was calling about the "same" issue as last time.)
Apple is playing the following while I'm on hold: Mark Ronson, "Uptown Funk" ... It's 11:15. CAKE, "Love You Madly"... 11:19, 11:23...
The representative got off the phone with senior adviser, he says the senior adviser knows "exactly what I'm talking about."
**** is the name of my representative--I asked him for it.
**** said his adviser said, "This is not really a problem with iTunes, and so not really something that can be fixed. It's just some settings "like cookies and stuff" that is resetting for some reason... You may be able to solve this if you uninstall and reinstall iTunes completely. But we can't guarantee that." (This is paraphrased, but I read it back to **** and gave him a chance to correct anything if I were misrepresenting him. He declined.)
I responded, "The idea that the background files ("like cookies and stuff") are resetting for a reason that Apple doesn't understand is not something I would dismiss as "not really a problem." It sounds like a pretty serious issue, something fundamentally wrong that shouldn't be minimized."
I asked for the name of the supervisor he had spoken to and asked to be connected to that supervisor. He said I cannot be connected to the supervisor because "we don't have that direct access here." **** wouldn't connect me with that supervisor directly or provide me with the name of the supervisor, nor would he give me any way to get directly in touch with that supervisor to ask followup questions. It is 11:32 p.m. eastern time. He is offering to connect me to a different supervisor.
My case ID is #1009753931. I'm on hold again.
It's 11:39. Back from hold. He says, "The senior advisers have gone home for the night." (Apparently they were there when he first reached out but had all left after I asked to speak to one of them directly... I have no way of knowing if 11:30 is the real time the supervisors punch the clock or if I was just blown off.) **** offered to have a manager call back at a time of my choosing. I told him I was hesitant because of my negative past experience. It is 11:42. I am asking one more time to be connected to someone else. He said he could set up a call back.
I asked every way I could think of (politely, if curtly) to speak to some one else directly. He stressed that the only recourse was to have someone call me back another day. I asked what would happen if they called back and I missed the call. He said they'd leave a callback number. I reminded him they didn't the first time (in December). He said "that was a tier one call." I said, "So for a tier one call, they hope you don't get back to them, but if you really insist upon it you will get a call back number?" He said, "That's correct."
11:45 p.m. Call over. They're going to call me back tomorrow at 8 p.m. I'll try to post again tomorrow night if I'm available to take the call. If I miss it because life is happening, we'll see if they leave a callback number.
I want to stress that **** was exceedingly patient and cordial. I have redacted his name because, prior to posting, it felt unnecessarily petty to call him out. (Even though I was frustrated enough to ask for his name and type it out at the time.) He was a nice guy trying his best to stick to his scripts. My problem is not with ****.
My problem is that Apple directs tech problems to nice guys who have to stick to scripts instead of technicians who would address the underlying issues.
I hope other users find this information helpful.