Eh I had 1 thief char, 1 barter char and zero lucky charm. I didn't do any respec shenanigans and I have a stupid amount of money (over 300k) at level 19. I was also buying minimum 3 new weapons every other level and then every level for a couple of my guys.
Suggestion:
Raise the attitude (with your Barter character!) of the merchants in Duskwood by giving them money or items. Give them about 100g and figure out how much attitude that is, then give the rest to hit 100. I screwed up and did this really late, so I could have had even more money. I suggest you sell to the merchants that don't sell gear (the two skill book ones, the fish guy assuming he has money, I think the matron of the undertavern, there are probably more). That way when you check the merchants that do sell gear it doesn't get clogged with your old stuff.
* Raising attitude costs more depending on the level of the merchant. The ones in duskwood are pretty cheap, I think something like 2000g for 100 attitude. The earlier you do it the more you'll make buying/selling from them. Later in the game merchants will be more expensive, but of course you should have more money then as well.
