It really wouldn't be a JP protagonist if they didn't let someone put them into bankruptcy to repay a really minor favor.
The artist has really done a disservice to the MC being a mysterious mage given the shortness of the hood. It doesn't really hide any of his facial features. Aisha is not blind, was within 3 feet of him, and is shorter than him so her line of sight would not hinder her seeing his facial features.
Also author very clearly has no idea how any organized labor union functions. A properly functioning organization would not allow two people to take up all the available work at specific levels while they have other people at that level available and looking for work. People join these union for reliable work that they can complete. You don't really want people taking on lower level work unless necessary because that's valuable experience for the lower level workers. This also isn't just harassment of the MC, unless they're the only 2 star adventurer there, it's harassment of every 2 star adventurer at this location. Imagine being put out of work to get by because a higher up is harassing one guy that's not even you. You wouldn't stay there.