Dude, once you max your masochism you'll be practically invincible... you'll be able to beat Bailey while doing literally nothing at all, so you'll be able to skip rent payments by refusing and choosing to fight them. Alternatively, once you develop the Stockholm syndrome for Eden, max your Skulduggery and Swimming and befriend the centaurs, you'll be able to submit to Bailey's punishments without suffering virtually any undesirable effects.
Not wrong but way too complicated.
You need a decent Science skill, B is sufficient, C maybe too, that could depend on physique and body build.
And you need a decent English skill. Again B or C.
The Science softens the first blow. The English gives you a powerful "Apologise". After that it's upon you to decide
how you want to win the fight you've already won.
If you pay attention in school that can be done within one week, ready for the first payment.
My Prime Directive is: Bailey does not get a single Farthing. Full stop.
And if they want to punish me then only if I have decided to let them.