Personally the money means nothing to me... The MC has a private beach, a beach house, and a car. He can then be with anyone he wants and never allow his dad to dictate his life ever again. If the MC needs money and isn't ready to be tied down then he could sell everything and travel or go back to school. To me the money option proves that the MC is just like his dad, picks material things over love.
As for wishful endings:
I would like to see the MC sell everything and buy two tickets to Paris, allowing the player to choose who he surprises with the second ticket.
Or an ending where he goes back to school and lives in the beach house with love interest of the player's choice.
Or an ending where he severs connections with Monica, Katie, and Jenna for a year, has Debbie and/or Lily maintaining contact with them for him. And then after a year he earns 1 million, receives the deposit, and walks back into their lives. Perhaps by throwing a "Dad doesn't control me" party in a new house that he has bought after selling the beach, beach house, and car.
None of those are really out there I don't think. Maybe even a "MC becomes a fashion model" ending would be nice. He does work out.