Why bother stealing gear? Buy it steal money easy fix.
Then why have unique gear laying around that can be stolen? For example, early in the game the shopkeeper Nebora has a nice pair of boots in her tent - an item that's far better than anything you're likely to own when you initially arrive to Fort Joy.
And yet, if you steal them and get away with the theft, the "stolen" tag remains making them impractical to actually wear.
So what's the point of them even being there in the first place? You can't purchase them, you can only steal them. But if you steal them you can't wear them without getting into trouble once you're caught wearing them.
Again, from a real-world perspective it makes sense. But from a gameplay perspective where theft is part of the game, and rogues exist, and stat points are spent on making them better thieves, it's a nonsensical design.
