I enjoy exploring those roads the Gazetteer identifies with dotted lines on my BMW 1150GS (a large and heavy motorcycle ideally suited for gravel roads but ill-suited for getting unstuck from mudholes and for turning around when the road suddenly ends). As a computer geek, I also enjoyed reviewing AOT centerline data with QGIS and various orthoimagery sources and get a particular kick out of finding incorrect data in the AOT data set. For extra fun, I did manage to put together a description of using AOT data to explore Vermont by motorcycle, including details on creating a Garmin map overlay with class-four roads and legal trails (for those not in Vermont, such things are legal rights of way but with minimal to no town maintenance; some are privately maintained and passable by passenger car, while others are so unmaintained that they're not even evident on the ground for a pedestrian. Most are somewhere in between.)
My primary interest in updating the OSM maps started with having a set of maps in Vermont that do include less-passable ways on the map, but that also clearly mark them as such. Most of the other available mapsets fall short in one or both ways, and many trend more towards removing ways that are not car-passable. As such, using my Garmin-formatted overlay in conjunction with the OSM mapset on my Garmin allows me to quickly identify town right-of-ways that are not on the map (or unmaintained ways that show as normal roads). Where those ways do not seem to be passable by normal passenger car in normal conditions, I've been marking them as tracks and using the Key:smoothness scale to distinguish between those that are a little rough and those that are more than a little rough.
Having since moved to Montana and then to Maine, I'm trying again to get some of the less-traveled areas around me mapped more accurately, with particular interest in the road and trail system. My dog isn't a fan of motorcycling, so I've spending more time on foot and trying to find public trails that are missing from the OSM map.