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Its a Thieves Guild
I've been letting my follower steal items; I'm asking do you ever have to pickpocket to complete the quest line since your follower cannot pickpocket for you.
It is definately doable to not steal anything. On the initial quest where you have to steal a ring and place in the dark elfs pocket, simply do something else unlawful and get caught by the guards. You can still progress through the questline. With the prev mentioned guild master job requirements simply do the forging quests instead of stealing items. Thinking about though, I don't think stealing the target items do register as stolen as it doesn't have the red steal interaction when picking up the objects.
Lol, my favorite jobs were always the Numbers jobs. I think I fudged books in just about every business in Skyrim. Great for quickly getting the work done. And I always like Devon more than Vex. You can get buy with no stealing. I did the guild to get the shout once. Surprisingly, the items in Litany of Larceny are not marked as stolen. Neither are the Stones of Barenziah, so yeah, I think they designed this questline so you didn't have to steal if you didn't want to.
Again, kinda doesn't make much sense, but maybe perhaps there IS honor among thieves. :)
In order to join the thieves guild, you have to pickpocket someone. In this case its to plant an item, but yes, it still counts that as a stolen item
Although that's the quest objective, you don't have to pickpocket anyone. You simply ensure you are caught by the guards doing anything else unlawful ie, picking a lock etc etc and after paying the fine the quest line progresses.
I actually follow this route as completing the initial quest means you have one less vendor in Riften.