Role Tokens not Falling Off
I had a Minecart Daredevil on the battlefield which my opponent had enchanted with a Cursed Role (I don't remember the card that they used for that.)
Later, I enchanted my Daredevil with a Young Hero Role from my Cut In. The Cursed Role did not fall off as it should have.
Shane Cummings#29616 commented
This happened to me as well. You can see in my shot my 4/4 dragon had a cursed role making it 1/1 but then had a Royal Role added making it 2/2 with ward 1.
[Deleted User] commented
Each creature may have 1 role from each player attached to them at once. Since the roles have different owners, they are both allowed to be on at the same time.