What I do is move the group close to a merchant, then separate my MC (a Rogue/Thief) from the group and have him go into hiding for the pickpocket action. Steal the gold which is easy, not the gear. As soon as I see the success roll, I close that window and immediately start sneaking away from the merchant and the rest of the group.
There is a delay before the merchant realizes he's been pickpocketed. By the time that triggers, my thief is far enough away that the merchant only starts a dialog with my other party members, standing there looking innocent. That's always resolved with a persuasion check, my actual thief character is never involved because he's too far away.
Fast travel can cheese it, but this always works and feels more realistic. It's basically the same mechanism as in Larian's previous DOS2 game, although that had a one-time pickpocket restriction per merchant. and per party member. They should bring that back.
