With all the stuff to explore i managed to never really check on this , so here goes: How do skills like Pickpocket , Gamble and Haggle work on followers? Do they work at all?
I have never seen or heard of anyone having them work. Although maybe if you have follower skills on, a pickpocketing follower may do your pickpocketing for you. I'm not sure about that though.
Tollo has never dipped a pocket for me, even when he was far better at it than my PC. They will spot & disarm traps for you, but even Franklyn Payne won't gamble for you.