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I'm unsure of that one, but a good work around where you don't need to use lucky is to get the gauntlets of thievery from the zhentarim hideout vendor in act 1 which gives you advantage on pickpocketing, reducing the chance of you rolling a 1 to 1/400 or something inane like that. Keep astarion as your main PP due to his bloodsucking talent imo.
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Unsure, but I do know that by the time you're level 10, if you've been pickpocketing, you'll have so much extra money you won't need to rely on pickpocketing anymore. I think the last time you should be pickpocketing would be the middle of Act 2, although you could reliably stop without any issue around the githyanki creche in act 1.
Guide to pickpocketing:
1. Use Astarion, stack dexterity to 18 (using cats grace armor to push dex to 20)
2. Acquire https://bg3.wiki/wiki/Gloves_of_Thievery
3. Pre-cast guidance
4. Smuggler's Ring
5. Have Astarion suck someones blood (no ♥♥♥♥).
You now have a ridiculously high chance of pickpocketing under 12 skill. If you really want to cheese, give the vendor you want to steal from around 3000 gold with Gale or some other wizard/cleric with feign death so they get friendly attitude, and then have them cast feign death on the vendor, making it so you can pickpocket literally everything without having to worry about failures.
pickpocketing can be buffed to sky high heights... lucky is as is but more a combat thing but problem with pickpocketing is you can't use rerolls like inspirations... so those 1 rolls are always a thing until you get Reliable Talent that's one of few things that are any good problem is it's so late that i wouldn't even call it an option.
Basically pure rogues need a buff something extra. like buffing crit range if you attack from the back and something dual wielding related that in itself need a bit of tweaking in vanilla game.
Like extra damage on chain attacks if both attack hit or something like that... as is i would avoid going beyond level 7 and even that's questionable.. Probably level 3. 4 or 5 depending on what the other classes are.