Re: Illegal Cross-Continent Road Race Hero
I like the idea of "checkpoints"; of places that have to be hit, in the correct order. You could place one or more in remote-ish locales, so that the competitors have to be good at more than straight-line zooming. Locations that require going on twisty, hilly, etc., roads would shake things up a bit; make the race more than a repeat of the Cannonball Runs (real and fictional).
However, the "must stay overnight" bit just kills it for me. That just doesn't fit the genre (more of a sub-sub-genre, really). It's no longer a long, hard, hairy slog from one place to another, but a series of short dashes, just 6, 8, maybe up to 10 hours at a time. It's a completely different feel. I can see some characters dismissing it as "nothin' but one a dem fancy-pants road rallies."
I'd recommend keeping the checkpoints, but just as someplace each racer has to reach to find out the next checkpoint. No disqualifying for reaching "late" (leaves the chance of "come from behind victory" open--good RPing possibilities there), and no requirement to stay in one place for X hours. You get to a checkpoint, prove you're you, and get the location of the next checkpoint. After that, you can stay awhile, or take off immediately.
This does mean a team of two (maybe more) with a car that's comfortable to sleep in has an advantage.