Reading through the compiled QnA answers made me realize why i had developed an attachment towards him specifically.
I believe it mostly stems from the consistency of his actions which offers stability despite how twisted it may seem.
Bailey isn’t nice, but he’s always there for PC no matter how annoyed or upset he acts outwardly, a constant presence in their life that’s unmistakably dependable (or suffocating and oppressive to some).
You meet him first in game and would see him on a weekly basis whenever he collects rent even after moving out of the orphanage—excluding Avery’s route.
He’d sell the PC off, but there are limitations to his actions, a personal moral code he wouldn’t truly cross if it’d permanently damage PC.
Even when PC crosses the line, there are consequences, but at the end of the day Bailey still wants them back.
It’s so compelling that he whole-fully believes that PC is ‘theirs’ even if it comes from a business standpoint first and foremost (or how he convinces himself), a marketable product that would always be under his control and radar.
Some pointed out that's the reason why Bailey acts so frantic when PC is sent to the prison island, as their authority and power are less affective outside of the town, unable to micromanage + observe his ward’s every move.
He's not the perfect guardian figure for PC, but compared to the others living in town, I'd say he could be categorized as someone who has the 'kindest' motive, especially since he's doing everything to strengthen PC (emotionally and physically), a harsh life lesson to prepare them for reality.
TLDR; Bailey is a fake idgafer who soothes my daddy issues by being present (even if emotionally distant) and dependable, thank you for coming to my Ted Talk
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