I failed completely because in my selection (US: Boston/Cambridge) there are multiple streets with the same name like Broadway and First Street, and I always picked the wrong one.
I know this is fundamentally an OSM data problem, but it's also your UX problem now. (N 42.5, W 83.17 if you want to have a look.)
Also it was quizzing me on park trails. And I just got an underwater tunnel at the zoo. I guess those are technically named ways in some manner of speaking, but they're definitely not streets with signs.
All that aside, this is really fun! Personal best 470/500. I wish I could make it longer; n=5 is a small sample and my scores vary tremendously from one run to the next.
I got one of those too, but I liked it. Nice to explore the major bike/pedestrian paths.
I guess it could be an option.