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The first is the starting quiz, some of the questions you get does give you more starting money.
The second is going to the library. Each different area gives it's own stat. Also, no matter what area you go, you'll have an event for the character you have the highest relationship with, so the person you get at the final question in the quiz will always be the first person you see.
The third way is getting it as a reward for a successful skill check but what stats you get is based on what event you get so it's always random.
And the fourth is hanging out with an NPC during lunch. During lunch, you have 3 tables that are always 2 love interests for raising your relationship between one, the cat girl for the shop, and a 5th table where you get +4 to one of two stats.
The Interdimensional Prince at lunchtime is the best option for money if you think you need extra money as his options at lunchtime always seem to have a +4 money option.
The Prince and the Coven both have two events out of three where they can give money.
Slayer, Coach and Wolfpack will never give you money.
Yeah I saw the lotto ticket online, so fat ive gotten veggies twice and poop guy (made a feed about it, if youve got it to go comment!)
I started going to the library after you mentioned it, and i won like 100000$ on kikstart then spent it all but 2$ on fee lol
and i havent seen the Prince at lunch yet, ive only seen him when i kicked his "armies" a$$ to keep my love demion lol
You're right that money seems to be rarely used for choices, I've seen it a few times for Miranda, Vera, and weirdly enough Scott. All in all I find money to be a much more valuable stat in multiplayer, where you can be locked out of your desired location.