I can see people's points but...
As for taking gold from trainers, that's not as easy done since the more you take the less likely it will work, becuase of this, its frowned upon picking raw gold over random jewelry.
As for pickpocketing armor and weapons, even if for RP it does not really do as much since most creatures you come across have poor armors and weapons. IMO poisoner is the only thing that feels fun at this point, but I would not even count that in the thief category since its for killing.
It seems skyrims idoiology of a succusful character is one who can devastate everything and kill, well and fetching items which usually leads to killing. Why can't a successful character be one who plundered to riches off the pockets(and houses) of others treasures?
I think NPC inventories respawn in 3 days, or the same time it took in Oblivion.
Been trying that on multiple npcs, so far it's not holding true.