NGL, this chapter was a dumpsterfire from start to finish. First we have Lotto who is not just an ex-noble, but also trained in both magic and combat. Why the fuck would someone like that be destitute on the side of the road?
Bandit or thieves guild master's favorite new pet mage I can see, but hobo turned porter for an adventuring team, utter bullshit. His arrogant ass would either turn murderhobo and kill them outright or press gang their asses into minion. I get the whole revenge on the past abusive asshat angle, but it doesn't fit Lotto's character, nor his abilities.