No... you measure in for the regatta two sails. One is your primary sail. Should you damage the sail the officials will give you your substitute for the next race on the water. BUT... you have to repair the primary sail and go back to that for the remainder of the regatta.
Sometimes... that primary sail simply Can't be repaired and you get to use your nice fresh secondary sail for the money race.
Johnny and Charlie will also use the flat sail (part of the program) IF they think the weather will give them an advantage.
Last cycle... they had a seperate mast program and the super duper Cuben Fiber sail material program with Mitch and one other team. It worked! and the US got Silver!
There are LOTS of ways to win... its a game and when the skill level gets really close you can get an advantage using the rules!