I would agree that making it a "race" adds another layer of complexity and hazard than "cruise". But two boats together rarely "cruise"....

Given average conditions on the proposed route, what would be the minimum reasonable craft that could make the journey in the designated time period?
I guess it would be ideal to have boats with similar capabilities, in order to keep the "fleet" in reasonable proximity to the support craft.
And I agree with Robi, I don't believe that our tax money should be spent bailing out the reckless and/or foolish who venture into something wholely unprepared. I know it happens, but I still don't like it..