Yeah, you get the bad ending if you don't win the award - you need fame 500 to win the award. Even if you do win, to get the best ending you have to visit him a lot during the afternoons to get the plot involving the red-haired guy and to get to the choice that makes the ending best or bittersweet. I think that scene is after six or seven scenes in his office, though it may be dependent on seeing scenes elsewhere.
Meyaoi mentioned elsewhere in here that they've gotten a proofreader, so probably it'll improve by the time we all play it again for the voices!