You will get 15 if you have 0 coffees or +3 otherwise. You can get free coffee (and medicine) by doing the Tutorial fight at the Fight Club as many times as desired. You will need lots of coffee and hankies.
As a rough guide, provided you are using Hyper Hentai mode properly, you will need Strength 30 to win a Grade C race, Strength 60 to win Grade B, and Strength 120 to win Grade A. Train at the swimming pool solidly twice a day until Friday Day 12, increasing your Strength and Charm and gaining money. Start with Strength 28, Knowledge 1, and Charm 1.