Update - 4.11.18 12:30pm EST:
I spoke with some high level technical advisor who's part of a group of technicians that apparently only report to the Executive Offices from what I'm told. He told me Apple engineers had made "some changes on the back end" to my account, and that I needed to:
1. Deauthorize all of my computers and sign out from iTunes completely on each computer
2. Turn off ICML and sign out from my Apple ID on my iPhone
3. Sign back in to everything and test
This worked for me, aside from the annoying part of having to redownload all of my music again. I asked what the problem was given that "something" had been done to my account specifically (that's what I'm told.)
Tech support: "The engineers don't share that kind of information."
Me: "Let me get this straight...the problem is resolved (for now at least), and you don't know what the fix was, and I'm not allowed to know what the fix was?"
Tech support: [long pause] "Yes sir, that is correct. I don't have any information on it."
Me: "So if this was something related specifically to my account as you say, how am I supposed to make sure this doesn't happen again? How am I supposed to know I'm not potentially doing something wrong? Or not doing something?"
Tech support: "Well it could've been a number of things, maybe something as simple as a song that was having an issue on our servers."
Me: "Ok, so again, that's important information for me to know given that I've been having this issue for 2 months now and would prefer it doesn't happen again...especially given the amount of time and energy I've dumped into this issue trying to get it resolved already. Don't you want to know what the fix too was so you can help other people?"
Tech support: "Yes sir, I do."
Me: "Great, so why don't you go try to figure that out and get back to me."
Tech support: "I will do that, I'll talk to engineering again, and I'll contact you back in 2-3 business days."
Me: "Great, sounds like a good plan. Looking forward to hearing from you."