I've been running with a very large Meetup group on Wednesdays since 2014, and I come often enough now that I'm one of the run hosts. This means that I get to sneak in an orienteering-style run twice a year. One of those days was yesterday!
and Checkpoint Questions
I try to keep the focus on the fun of finding checkpoints, so there are no time limits or point values. The map is just a screenshot with LIDAR contours on top. People can run in teams as large as they want. There are street names on the map (which, after hosting five of these now, is the most important thing I've seen for lowering barrier to entry).
Anyway, everyone had a really, really good time. We went out for beers afterward, and several people were interested in attending a more formal urban orienteering later this month (a Street Scramble). If you're in Seattle, I'm planning on doing another one on August 2.