Like, I get the sentiment, but with what's going on in that restaurant on the sexual side - I'm pretty sure growing up with a relatively inoffensive, depressedly drunk dad would be about 20 times less traumatic. Not everyone is a natural perv like Akari. That's if we ignore the whole age factor.
What I can see, tho is the MC altering the deal somehow, probably starting to pay an actual wage to Catherine, while either wiping off the debt or keeping it strictly for "fun times". Like he can pretend all he wants, but his hero complex is already at "white knight" level. Or maybe she would become the new waitress and he can just buy an industrial dish washing machine and a bit more plates - that's how it's done in most restaurants where I am.
And I'm pretty sure Catherine is gonna get to girlfriend before Hannah - unless something out of left field just jumps in, I don't see Gilbert switching sides before the time-skip.
Now that's an interesting possibility, tho I'm not sure how smart it is from the political side of things. I'm willing to bet that (or something similar) was what his grandpa did and how he ended up outmaneuvered by Gloria. MC should learn to play the game, not ignore it, otherwise he'll end up in Reggie's position sooner or later.
As less traumatic as it is. The kids are going to become a regular site around dinner time. Since they don't really have any other option for food. And as soon as Lucy finds out she is going to want to help. Since Regi isn't an aggressive Drunk they wouldn't need to move in. Agreed on making things better with Catherines job position. But not really an easy way in the short term to fix the money problem. I can see Lucy hijacking the little sisters to test her baking on.
As much as he needs to learn the family stuff. The MC hates learning. Why Lucy does his homework. And he keeps hating seeing the various information packets Alison gives him. He has to deal with business paperwork that he hates doing. As much as he needs to doesn't exactly mean he will do it.