I find there are 2 things wrong with stealing:
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When just following the quest lines, it is impossible to get lockpicking up high enough for the later missions without grinding a gazillion of locked chests. You basically are forced to go on a “thieving spree run” all across the place. Even with the millers teaching. Problem 1) Feels very grindy. 2) This alone yields so much money that the missions feel meaningless in comparison. And maybe the player does not want to be a “thieving scum” that opens any chests they can find.
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If you decide to roleplay a real thief that also steals from the poor, ok, but here still the overall profit is way too high. The reward is insane and the AI is not intelligent enough to really be a problem. Within 2 hours you have several thousand gold. Combine that with a horse, and even the carry limit while stealing is no limitation anymore, as you can directly teleport the stolen goods to your horse outside.
Solution:
-Missions should not contain very hard containers
-General loot in poor peoples chests should be much lower in value
-Optional: Dont allow moving items to horse, if its not very close.
). I try to play the game & not over analyze it.