I love the idea of some trail or rough road competition, but riding a street-bike-with-dirt-bike-aspirations, namely a Wee-Strom, you guys with for-real dirt bikes would walk all over me
What about something along the lines of Equinox to Equinox Rally
but based upon geographical points (McLaren Pass, the Arctic Circle sign on the Haul road, GPS coordinates of some point on your favorite single-track trail, etc.) over a shorter timeframe (one weekend, an entire week, etc.)? The farther/more difficult it is to reach a given destination, the more points it is worth; most points at the end wins (since it can't be based on speed, if we are using public roads). Proof of completion could be done the same way as the E2E, or by using a smartphone or GPS to create a KML file to log the trip...
Just an idea.