I¡¯m going to skip the whining about how poorly this is implemented in Mail and go straight to the new ¡°lesson."
You can¡¯t enable VIP ¡°status¡± for a send in Mail unless the email address is in your contacts. Not just the sender, but the email. AND it may actually be in your contacts but apparently Mail can forget. If you try to enable VIP status, you won¡¯t get an error, or any indication that ¡°adding¡± won't work, except for the fact that it does not.
So if this happens to you, right click the sender in Mail and select Add to Contacts. In my case, this changed nothing in Contacts (the email was already there), but it unlocked the VIP status.
If anyone knows how to directly access the VIP list, I¡¯d dearly love to know!
Cheers,
tod