Save right before you try it. Give the target some kind of clothing/armor with a higher DR rating. Wait.
When the target “equips” the new clothing/armor (you may have to “wait”), now is the time to pounce! Pick-pocket again for awesome results!
It should work, the same concept works with weaponry. But, watch out for ammo. A caravan only needs “one” of the ammo type for the new weapon given, they will perpetually “replenish” ammo.. Followers I’m not so sure, I never use them.
I have never heard of this "reverse pickpocketing". i mean, i know what it is, per say, but is there something to it that is helpful or beneficial? if there is, i would be grateful to know.