To answer my own question, based on all the responses, thank you everyone, here’s what I’m thinking.
Get a number of different colored d20s, one for each race team. At each leg of the race roll them all on the table for the players to see. Any 1s are automatically knocked out of the race, they had some catastrophic failure. Any 20s get a marker to indicate some great success or inherent skill that will grant them a bonus later.
Then in the final portion of the race I’ll take the three teams with the most markers and put them in scene in direct competition with the Players. I’m thinking this will allow my Player’s to go hunt teams that are doing well to take then out before the final leg if they want and let them see how dangerous their competition is.
Wikipedia says the virtual memory cards are compatible between them. But I’ve never done anything with the Memcard Pro. I have messed around with PS2 memory cards and PCSX2 and generally the raw bytes are compatible between the two. I would imagine the M.Pro is the same.