Well, I can say to you the idea is very old

I had it once too, and that time the MT was not happy with the idea.
My idea was to make a track, which consists of not gates, but airports, and/or NAVAIDs. The course could be a really challenging track somewhere in a rocky area, with given altitude and maybe speed limits, delegated airports for touch-n-go, and on the course, you should go from NAVAID-to NAVAID, or from airport to airport. Maybe 10 waypoints on a half hour "racertrack". I selected the Norvegian coastline which has a tons of Fjords and lots of hidden, dangerous airstrips in FS.
But for all of this, we need a special version of FlightLogger. At least a feature is a must have: it needs to know where the plane is. It should lookup everytime, which waypoint, or coordinate the pilot is closing, so it could do a tick to that leg in your racing flightplan. Also it should judge the total time you take on the course, and should give the special penalties if you miss a rule. As this is a little hard to do, the idea was trashed.
I think a very easy method would be enough: a script that can calculate your total time took during a tour, and a tour that is consists of difficult and dangerous legs. Of course it may give the chance for cheating, but we are gentlemen anyway
