Not everyone likes Old & Ugly. The dev apparently doesn't either. He's very keen on making all the LIs look good.
The Hobo has a lot of fans. In the case of this game, I can even understand that, to a certain extent I like him too. And I'm keeping my fingers crossed that guys get what you want.
However, it might not be easy to write many scenes with him. The father-in-law on the other hand is part of the family, so he has easier access to Kath, which makes it significantly easier for the developer to write good scenes. In contrast to the hobo, who has no connection to Kath at all, he always appears like a devil in a box. Here, the dev has to put in a lot more effort to write scenes. However, he has already proven more than once that he is very talented at writing good, crazy scenes.