I thought in-system races might possibly be made 'fun' using 2-person kit craft built onto high-power, volatile liquid-fuel rockets, which burn most of the craft's fuel getting it into a high velocity; starting from the insystem, it would have to use what little maneuver fuel it has left to slingshot around anything ranging from a moon to a gas giant, and return to the starting point.
If you want to inject some space opera into it, make the course pass through a "Star Wars"-type asteroid belt.
That leaves lots of room for added risk, capitalizing on different skills to compensate. Mass is a critical factor. Nastier fuels, faster or slower burn time, less (or more) structural support, piloting skill, mechanic skill, even gravitics skill can play a part. Even, perhaps, a controlled amount of allowable sabotage.