Join the "Debate Team." It sounds boring, but the Debate Team skill tree unlocks "Gaslighting," which is the only stat that works on the Landlord character (Mr. Henderson) to lower your rent.
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Avoid the "Pre-Med" track. It is a trap. It requires 300 hours of grinding with a "Boring" status effect active the entire time. Instead, go for "Philosophy Major." It has the highest Sanity recovery rate and unlocks the "Sarcasm" weapon in dialogue trees. Join the "Debate Team