As for Alison, this is probably a "there's no arguing taste" situation. As for the company that owes her money, that is her former job. It doesn't stop Alison from seeking employment elsewhere. The whole reason Gillian cheated on Ian was she moved to another city to find work. Alison even admits that she doesn't care that her former boss was a crook. It doesn't matter to her that other people were impacted. All that matters is that it affected her. If she's able to spend as much as she did on her vacation, she's able to put down a security deposit and a first month's rent on an apartment elsewhere. We're not even sure the nepo baby is useless. We just have Alison's word for it. From what little evidence we have, the nepo baby was more competent that her replacement since she never called Alison on her time off to fix an issue. And who is the love of Alison's life? It isn't Milo. I'm not even sure what happened there. In the first conversation, it says he dumped her, but every other interaction, including him accosting Ian and Jeremy, imply the opposite. It isn't Ian. She just sort of goes along with his advances. She enjoys spending time with him. But she is just as happy to go with Jeremy instead. The closest thing to showing genuine emotional affection she does is trying to cook Ian dinner. In my opinion, Alison is the single most passive character in the game, happy to wallow in her own misery. Actually, thank you for allowing me to talk it out because I can now pinpoint my problem with Alison in one sentence: she is the only character that seems content to wallow in her own misery.
To be completely fair, though, a significant portion of my opinion of Alison is likely due to burn out. I wasn't interested in pursuing Cindy due to her relationship with Wade. I wasn't interested in pursuing Emma due to liking her better as a friend. I thought Cherry was boring, and I have next to no interest in the type of relationship Minerva represents. With those characters, I did one, maybe two, playthroughs mostly to unlock their scenes. That meant that Alison became the default early-game LI for the majority of my playthroughs. I ended up spending probably more time with Alison than with any of the other non-protagonist, and each time I read a scene with her, my reading of said scene became less charitable. I will also say that what I said about Wade applies to Alison. I just want her to actually want something or do something, anything, proactive. If she does, she'll earn a ton of points in my eyes. The game isn't over yet, so there's still time. Even if she doesn't, I'll still consider her a good character. She does fulfill her role in the game well.