I just got road tagging working. It took a bit of doing but now we can not only upload tracks from a GPS or plan routes using waypoints, we can also select individual roads and tag them. 

For instance, I've tagged the White's Ferry Road with "Pavement Ends", (a marker I included just for rshaug because we know how much he likes taking the Ninja off-pavement). You can describe a road, tag it with a growing set of icons, rate it and add some tags (useful for searching):

I've had to rewrite all this stuff three times now, which is why it's taking longer than expected. But so far, it's looking like the technology choices I've made this time around are actually going to work. 
We won't know for sure until we actually start using this stuff to plan trips, document rides and tags roads in earnest.