Been a few months since anyone mentioned anything, but here are my 2 cents.
The smaller groups is a great idea. Even if we all have to do the same trail, just have them start 30 minutes apart
Have 2 or 3 trails for the 101. The normal 101 trail that was used for the last 2 years, can be considered Intermediate to some. So maybe make the Top of the World run a Beginner trail, as even a stock Jeep with bold tires could make that trail with ease. As for a Advanced Trail, well, my Jeep is still stock, so you can pick it.
Provide a Map, custom made by the Jeep Club, that shows where these trails are. And maybe even color code them like ski hill runs, Green for easy, Blue for intermediate, and Black for advanced. Must people would understand those colors as difficulty levels. And if they don't, they'll learn.
And finally, make sure to mark the trails with the correct colors at the beginning of each trail you pick, so that no one accidentally goes into a trail that they don't feel comfortable in.
Those are my 2 cents, other then that, I think you've done a great job so far Waytec. Can wait for next years 101.