Penalties and everything tend to be assigned at player discretion since RNG will be determining winners and course completion at all is what's needed for the Retrospec item - so in short, up to you! May can get away the whole course without a penalty or she can be docked for not breaking a sweat because that shit's suspicious. Whatever's more fun for you to play since we're not ICly keeping track of points or anything.

Hopefully that answers the question? It's pretty up in the air but it's really whatever's the most fun option.