Santa Monica / Westwood
Go outside and play (games)!
Me 10 years ago. Should I update?
... fail to score 55 points in the second game, do you start from the beginning and try to achieve 50 points again?
I wouldn't want to play that way. After failing any game, I would just try again to reach the required points.
The only reason I would start over is if I found that my 'permanent' professions that I selected in the early games were not helpful in reaching the ever-growing point requirements.
Additionally, if I didn't like a recently selected 'permanent' profession, I'd roll-back to the game it was selected and play that game over to get a different profession ... like returning to a save point in a video game.