I apologize I didn't mean to not show work, I just found it difficult/awk. to put my scratch work into words.
Taking your hints I still get stuck..If I use HCl then I will break the double bond and I will have the chloride attached, I could eliminate this and then use oxymecuration to get an OH and methyl both at the top, but then I don't know how to remove the methyl group.
And in terms of free radical bromination I run into the same wall.
I hope that makes sense as I may be trying to approach this problem the completely wrong way.