As everyone else is suggesting, the Bar Brawl Tier 3 Rematch is a great place to not only get the pictures for the achievement but also Torgue Tokens. I did it about a dozen times and got 3 pictures and at least 100 Tokens. Also a pretty good place to level up a character in Normal Mode if you're too lazy to beat the game and farm The Warrior and/or Terramorphous, albeit more time-consuming
As for losing money, as Mr. Torgue would probably say, WHO GIVES A F*CK?! But really, you can just dupe money like you would with weapons, but other than buying ammo, what's the point?