The situation with Bobby is a very interesting one.
On the one hand, Bobby seems to genuinely love Lori and treats her kindly, and she does seem happy with him (at least, I think so). On the other hand, let’s not forget that he was willing to throw their relationship under the bus just because his younger sister had a fight with Lori’s younger brother. And it’s not like Lincoln hurt her, beat her up, or did something truly cruel. He simply spoke unfavorably about her to his friends. (I don’t like her, so maybe I’m a little biased.)
Is that really enough to ruin a relationship? For Lori, clearly it wasn’t. We can speculate about why. But if we look at this from a slightly more pessimistic angle, it suggests that Bobby has no problem putting his family’s interests above his relationship with Lori. That would be a good trait if we, as players, were part of Bobby’s family.
But we’re part of Lori’s family—so for us, that’s a bad sign. Realistically speaking, what if Lori were to have some kind of conflict with one of his relatives? Or if someone in her family clashed with someone in his? In cartoon logic, of course, everyone basically gets along, and conflicts only pop up for plot-driven reasons. But if we approach this story a bit more realistically, the large Loud family would probably have some kind of run-in with the large Casagrande family sooner or later. Would Booby then go back to being an emotional terrorist?
So ultimately, I’m not saying Bobby is completely bad. He actually reminds me a bit of Jerry from Rick and Morty. But I am saying that I’ll personally keep all of this in mind when deciding what to do with him.
P.S. Honestly, though—he’s kind of weird in a disturbing way.