Attempting to steal an object a person doesn't have should still make a stealing roll with the usual chance for failure, as the only way to figure out a person didn't have something would be to go fishing in their pockets.
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The problem with playing a dip isn't the mechanics but rather people playing one and getting caught a million times within their first month because they don't understand UE and character progression. I like this idea, and if there was a way to codedly support it that wasn't a hassle, I'd be all for it.
I've seen several people playing pickpockets who just go around trying to rack up a high score.
If you're playing a combat character you face consequences if you just try to murder everyone you meet. If you're playing a decker, you'll face consequences if you try to hack nodes willy nilly. This is how you learn the game.
One of the most fast growing characters I know was a dipper, to say it's a sub-optimal strategy just means all you're trying to do is dip people's phones and wallets in the streets.
From knowing this other character I can assure you there's far more money to be made from stealing than just that.
Regardless of nerf or buff, I agree with Vera here, just for the sake of realism.