And, with your OSM updates, next time the city is re-processed by CityStrides, those manually completed streets will become non-manually completed (I forget the proper term).
I also seem to recall a wiki here, about getting started with OSM. Found it!
PS. There is also an Beginners’ Guide and an automated tutorial at OSM. As I recall, once you sign up, it will ask if you would like to see it. If doesn’t, see this: Interactive tutorial to getting started editing OSM - OSM Help
Oh, and you can also upload GPS “traces” to make adding roads and paths easier, when no satellite imagery is available.
Warning: Getting started with OSM can be very addicting. You might find yourself correcting all sorts of things… I started adding all the drinking fountains in local parks!