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if you get caught just go invisible and run away. then you go back to stealing right after
Why am I imagining him collecting protection money...?
I'm not sure what you mean.
Pickpocketing can be tedious at lower levels. You gotta juice Astarion - let him bite you, equip him for theft, split him from your party, maybe use Minor Illusion, etc. If you pickpocket on a random basis, your entire party will most likely be there and it's a major pain to extract all of them from a Temporarily Hostile sitch.
Once you get to Baldur's Gate, Astarion can execute the Great One Day Heist taking every valuable item from every merchant. You'll then be well equipped and have maybe 40K gold. Then you can just buy your daily consumables. And then you can drop Astarion for a more powerful late-game character.
(sadly they nerfed the ability to knock down vendors and steal their stuff, but its still useful):
- cast a cloud of darkness. go into turn based. start pickpocketing. profit
-If the vendor catches you, have your party knock them down with non-lethal. return after next long rest. profit
-the cloud also works to steal stuff around from containers.
So many ways to cheese the game lol.
This is until they also change and flag Darkness to be a hostile spell (which totally should be)
He is, but you just to come to the dark side young padawan :)
Doesn't matter that he is near too many people.
Park your party around the corner.
Put on the gloves. Cast guidance on your thief. Go invisible.
Go make Dammon your beetch. After you steal a few items go back to your party and wait for the guards to leave after he starts whining about a pick pocket. When guards leave, go sell him what you stole or steal more off him.
The problem you'll run into is finding merchants with enough gold to fence your stolen goods.
Don't worry, I robbed Arron blind as well. Same with that little toad in the druids grove, same with that half orc in the underdark. I own them all!!!
The ownage begins in Baldur's Gate when your expected pickpocketing result is 26+ +/- 2. That almost guarantees success for any 30 DC attempt.
I played my Ironman Tactician run without pickpocketing. But damn, pickpocketing makes the game much much easier.
then collect and sell everything from enemies. armor of value, weapons of value, unwanted scrolls that you will never use.
hell if you dont use alchemy I remember selling like 20k worth of gold in alchemy ingredients during act 2.
also make sure to sell and haggle with your highest charisma character.
should be rich as hecky by the end of act 2.
EDIT 1:
also keep on the look out for things that are small but worth a lot.
early on a decent stack of incense or ink wells that weight practically nothing can get you a few hundred gold on their own.
I remember picking up like 30 incense candles and they sold for a fortune lmao. yet weighed like 2lbs altogether.
EDIT 2:
also remember that merchants restock on level up. use this to sell en masse when they have low funds.