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I also found it very hard stealing from the people in the square, but there are plenty of people you can steal from in undertavern....
fighte when you are walking up to the ruined sorc wagon there is a 2 handed axe in the chest. After that your next big upgrade you can get is lohar hammer which has 20 percent crit. You get that after finishing mordus which should be your first stop. For a bow your best bet is the lute merchant who is a lil ways from where siva is hanging out. You need high persuade but if you succeed she sales bows that can have like 20 percent crit on them . Enchanter sadly you will have to buy that one.Good idea would be to journey to jahan he normally sells better caster gear than what you can find at driftwood and if you have 4 thieving you can rob him blind quite easily . Scoundrel I believe the arena lady drops some great daggers. IF not her the annoying dwarg guarding the underground entance has good weapons and is easy to steal from. There is also ethne a undead merchent who is south of where jahan is at. She sales a great belt and is alone so easy to steal from.
Lastly there is a dwarf begging for money if you flirted with butters or at least talked to her she will give you gloves with 2+ thieving which will make your thieving life alot easier lol