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Ya. Thieves guild just trains Pickpocket, Gun, Greater Evasion, and Marksman. The normal Derphy trainer does Lockpicking, Spot Hidden, Disarm, and Magic Device.
This is correct, you just get 2 vendors in the basement that sell stacks of 10+ lockpicks pretty regularly, though some other city vendors have a chance of selling them as well. You can passively join by just talking to the guy at the door nabbing the quest and just passively steal stuff from delivery quests is all i'm saying, theres no reason to go out of your way, you dont "need" to unlock it, though it's "free" if your gonna steal nice stuff from those quests when u come across them.
Or go on a grand quest visiting every town and selling your tush.