I'm afraid that if it is in the form of a
speed contest/Cannonball Run, then obviously the Pilot with the fastest Aeroplane is most likely to win!...

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...my usual, Touring, General Aviation, Piston Props would never stand a chance!...

...!
There would have to be another way of arranging the flight(s) into separate groups/types of aircraft?
It would have to be a short, 1 to 2 Hours duration, Hop from A to B each Weekend to complete the journey.
From past experience, I find that most Sim Pilots get bored after a short while, and either leave to watch the Dreaded Football, etc, on the 'Tele, or fool about, and annoy others with various Aerobatic, etc, stunts, (and then go off to watch the Dreaded Football, etc, on the 'Tele)....

...!
The usual type of our pre-arranged, shortish, Weekend Tours, from A to B, over the total distance, works very well, and suits most enthusiastic Multiplayer Simmers...

...!
...so...there you go...
Either a Race, from start to finish?...
...or a Tour from Start to Finish?...

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...my four Pennyworth!..

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F...G-BPLF....FS 2004..+..FS Navigator... 8-)...!
Win 8.1 64-bit. DX11. Advent Tower. Intel i7-3770 3.9 GHz 8-core. 8 GB System RAM. AMD Radeon HD 7700 1GB RAM. DVD ROM. 2 Terra Byte SATA Hard Drive. Philips 17" LCD Monitor. Saitek Cyborg X Fly-5 Joystick. ...and a Briggs and Stratton Petrol Lawn Mower.