Hey, look at this ask I totally remember getting but then never answered. High fives all around.
For the most part, Fortune is happy. His business is going well, his nieces are cute as buttons, and he’s married to a woman he loves. There’s some conflict between him and Saviero that I think probably causes him to drink a little more than he should. There’s also this sense that he’s betrayed his family in deviating from the life they laid out for him, but there was little else he could do when Koina burned everything else to the ground.
Overall, his new business makes him happier, though he still feels the weight of his forefather’s expectations. I think that with time that will begin to fade.
There are a few other things that I think would bring him happiness (children! who’s surprised), but that’s never really seemed to be in the cards for him.