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Whatshisface on the ship is a good investment for equipment since he’ll stick around longer, but the guy in the undertavern is probably the best equipment merchant in act 2.
I bribed all of the merchants in the square as well. Act 2 is the longest one.
I'm at over 200k gold at the start of Act 4 thanks to a combination of boosting attitude through gifts, as well as stealing from NPC's who I fully intend to kill anyway (and pretty much ONLY NPC's I intend to kill).
The human merchant also sells Warfare and Huntsman books and has a couple of vendors near him who sell skillbooks for most of the other schools. The fish vendor there is a good one to sell all of your garbage to since he never sells anything useful.
The dwarf in the Undertavern has a huge selection of weapons and armor for anybody, well worth bribing and checking regularly.
And is there any difference between giving a merchant gold, and giving them the items worth in gold? I guess it's best to give them gold first, so that you can then sell the items at a higher rate to that merchant later?
Overall though, it is definitely worth it. Attitude doesn't affect cost nearly as much as barter skill, but if you combine the two, it works wonders. Get a few pieces of barter gear and you'll be buying and selling for over 50% discount/markup. Makes that divine armor base price of 40,000 not hit so hard.