Sorry for the lengthy reply, but some people may want all of the info. I had a chat session with Apple CS this afternoon to answer the questions I had (AM vs iTunes Match). Apple CS responses in BOLD.
1) If I let my iTunes Match subscription expire, is my owned content still protected or, if I blow away my Mac and reload it from scratch, is all of the downloaded music part of the Apple Music service and going to be blown away if I ever cancel my subscription?
Okay, so you are more concerned with music outside of iTunes like on a CD or a third party music location that is not purchased within iTunes?
Okay, that is really great question you have! So when your iTunes Match subscription does expire, you will no longer have access to the “matched” content. So with this being said, I would recommend backing up the information that is not purchased within iTunes Store. However, you do have 90 days to see the content you have uploaded/downloaded through Match. This also with Apple Music as well. But we always want to encourage backing your information before transitioning over.
iTunes Match is DRM- free as for Apple Music it is DRM protected.
2) Is this by design that I can only play one device at a time??? I DON’T have that limitation with my iTunes currently. I was able to have up to 5 devices activated with my iTunes - why am I being restricted??? (use case - I go out to run errands and a friend is at my house enjoying my music - as soon as I start listening to music in the car, he’s going to get kicked off).
If you were to swap to Apple Music, you can only use one device at a time without the interrupting. But if you left the house like you mentioned, your Mac will see the screenshot you sent me above and your phone will pick up on another song.
Ok, so a single user account is limited to a single session. Does that mean a family account, while allowing up to 6 members is also limited to 6 devices concurrently?
It would indeed be limited to six devices as it matches with the Apple ID’s you are using. So if you have an iPad and an iPhone, you could technically use 4 other devices if wanted. But that would be the limit.
Right, so if all 6 family members were using it and someone went to use it on two devices simultaneously, they'd get the same message that I sent you then, right?
Correct! Since all 6 were being used, you are right.
3) My iTunes Radio stations that I’ve created now appear in my “recently played” list - how big can that list be and, if every those stations aren’t in that list, how can I retrieve them?? Will iTunes Radio continue to be available as part of iTunes Match? Is there an expectation on either service being end-of-life’d by Apple???
From what I can tell, the radio seems to be sticking around for quite some time as Beats and Apple sort of merged and this is a huge thing for them! The iTunes radio stations did get moved to “recently played’ s you are correct. Currently I have a colleague that uses it he has 20 plus stations on his “Recently Played” but this is everything he’s created.
There’s not a definitive answer on how big/much the stations can go to actually.
It will, since radio has been around before Match; this will not change. Match just allowed the skip feature more like a third party subscription like Spotify.
4) After finding out all of the above, I decided I wanted to cancel my AM trial immediately, to restore my functionality (so I can have my tunes in the house and the car at the same time).
Guess what? You can't!! (I've escalated the case, going to call back tomorrow - ran out of time this afternoon).
If you want to cancel your Apple Music membership, turn off Automatic Renewal. This will be the only way to cancel the subscription to Apple Music.
So, that's all you can do currently. If you sign up for the trial, you're stuck with the experience for 3 months.
Let you guys know how my escalation turns out - or if I have to wait 3 months to get it back.