I've had this idea bouncing around in my head for a while. Your city isn't that big. You've had 50 alleycats and they seem to keep using the same checkpoints because there's only so many bars/shops/people with houses downtown. You need something new.
So you get someone who doesn't live in your city, someone whose never been there, to design your route. Set them up with a map and some parameters (max distance, really, really bad neighborhoods, etc.). They set out 10 or so checkpoints completly blind. Whatever looks good to them on the map. Maybe they'll send you up the hill everyone hates or you'll have to find your way down the worst street in town. Maybe the checkpoint is in a mall or an office tower or the fastest way to get there is the subway.
Maybe it'll be the worst race everyone has done. But maybe it'll be awesome. And everyone can race b/c no one will know the manifest before hand.