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A small suggestion

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.

Playing a dip is already unappealing because of the troubles they have to go through and the enemies they can quickly make. This just makes it ten times harder for them. SD isn't always about realism when it comes to mechanics.

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.

Huh. Always assumed that trying to steal something that someone doesn't have was still a theft attempt. Had no idea. I am completely behind this one. Same for using pickpocket on someone who doesn't have any chy on them - if it's not already the case.

+1 with this. How do you know they don't have a wallet in their pocket? Because you slipped a hand in there looking. Should be a roll for them to have noticed you were poking around in their pockets.