Biweekly, monthly, however often, have a script randomly select X number of streets in a given municipality. Have selection criteria such that the shortest route connecting all X must be less than Y distance (8-20 miles perhaps, depending on the difficulty). Users would have to ‘submit’ their activity to the challenge, which would then determine if they hit all the nodes for the streets of the challenge (I guess this would be necessary because if you had previously run a street in the challenge you’d no longer see street data for that run).
A limitation is it would have to be done in major cities with multiple active CS members, but if it’s demo’ed in a highly active area could be fun for people of varying levels of competition. Or maybe not; perhaps it could be auto-generated by user request for a certain city or zip code.
The competitive aspects could be who completes all the streets in the shortest time and/or shortest mapped distance (most efficient route). Of course there are mapping algorithms available but this would be on the honor system like so much else, hence ‘orienteering’. The non-competitive aspect would just be completing the challenge or not, and having yet another motivation to run streets you may have already run before, but only once or twice.
Apologies if this has been suggested before, it can’t possibly be that novel an idea, right? Just seems to me it might not be that hard to do at some point in the future when lifemap/sync/OSM/etc. are all solved.