I just got the Beasts and Bandits expansion pack and after reading the card "Guild Boss" I'm puzzled: It doesn't do any damage but lets you lose 2 Gold if you fail a combat roll. Before combat you can pay 4 G to defeat it and the reward is any one item from the market deck worth 8 G or less.
For me the card reads practically: pay 4 G to receive an item worth 8 G and get 3 Exp... And if you cant pay the 4 G, no worries, the challenge doesn't do any damage anyway.
Do I miss something or is this challenge more like a free item card?
1) Remember that you don't need to take damage to fail a combat check, you just need to roll less than the given value in a particular stat category. That's a common consequence of failing a check, but it's not required to count as a fail.
2) I don't see any reason combat would end after failing one combat check, so if you were stuck with only 3 gold and not able to pay him off, you might end up losing it all before you defeat him or escape (or more if you choose not to pay him off.)
3) It's unclear based on what you wrote above, and I don't have the card in front of me, but is the reward for defeating this guy ALWAYS an item from the market deck, or is that only if you pay him off? If that's always the reward, some people might choose not to pay him in order to try and get the item for free. Depending on how well they roll, they may or may not succeed in that venture.