Whilst I agree that NPCs probably react a little fast in some cases, you're meant to be a rogue. The best strategy is to, you know, not get caught.
When pickpocketing, cast Guidance for +d4, Cat's Grace for Advantage, then (and this is the important part) enter Turn Based Mode. Now you can steal as much as you like and no-one will start reacting until you end your turn.
Then, Cunning Action: Dash (twice if you are level 3+) and get the heck outta there. If you're still fairly close you can end 1 turn and move another 30+ meters away.
If they cannot see you or your party when they notice something is missing, they will shout for a guard, they will then both look around for a bit, and if they see nothing they will return to their default status.
On a further note, steal difficulty is related to weight. It's a LOT easier to buy armor and then steal the gold back than it is to just steal the armor.
When it comes down to it, the game is DnD based. You have to think about what resources you have available and then use all those tools to achieve the best result.
Last edited by Elessaria666; 17/01/23 03:19 AM.