Unfortunately there's no annual family plan subscription, just the month-to-month price.

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I had this exact same thing happen to me. I have 6 people on our family plan. None of them showed apple music after purchasing it.

I don't know what happened, but there must have been some disconnect between the family plan and those on the family plan. I had to remove and re-add each person on the plan. Then sign out of apple music and sign back in. Once I did that for each, it finally worked. I'm guessing it's a bug somewhere on the Apple services side.

I'd be curious to know if this is the same issue you're running into.

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Exact same problem as you stated. I think the problem is Apple has two conflicting software rules on their respective iPhone and Applewatch. iPhone seems to require “Family Sharing” feature to be used to share music etc but states that the same Appleid must be used for that purpose in the fine print 🙄 The cellular capable Applewatch requires “Family Setup” feature to be used so my son can have his own phone number, however it requires him to have OWN appleid. Same deal with the Applewatch app that is required to manage the watch through my phone. The Applewatch App is significantly flawed and NOT showing all apps, features and in-app settings, even though I am the one managing the content of the watch as the “family organizer” (with my new iPhone SE). Three hours on the phone with four separate Apple “Geniuses” and NONE of the techs could identify how to fix the problem let alone understand what the problem was! Apple should be brought to court for false advertising as the cellular watch is NOT able to do what they promise in their advertising and functionality of the cellular watch is severely limited if all it does it talk and text (should have just bought my kid expensive walk-in talkies or a sat nav phone - would have been cheaper!😡 More on reddit.com