I didn't understand the "test" the merchant did. "I sent you to a super expensive inn/brothel without letting you know, and because you paid I know you're not debauched"? Did he maybe mean broke? Because he wasn't broke before, but he just blew half of his severance pay in one night thanks to that merchant. And he basically is saying "I wanted to know if I could mooch off of you, I'll leave the moment I smell you're poor". And the MC is all "sure, you're a trustworthy guy I can use to rebuild this ruined territory".