The loser curates a public 100-song playlist about losing, failure, and regret under their real name, with a written explanation pinned to their profile, and shares it with the league. Song-by-song annotations are the deluxe requirement. It must stay public for a year.
Budget note: this one costs nothing but dignity, which makes it a strong pick for leagues that would rather spend the pot on the champion than on the loser's downfall.
Seen in the wild: fantasypunishments.com