Any advice on apps that facilitate the "Walk Every Street in my city" thing? Ideally just something where I could mark that I've walked a street, or perhaps better can mark that I have walked it, or biked it, and so on.
I use Strava to track walks, then import the data into the CityStrides website. They work well together.
Route planning is tough, even with automated helpers like Every Street Challenge (http://www.everystreetchallenge.com/). Automated ones don't take into account things like being able to cut through a park as a short cut.
Usually for route planning I pick a chunk of streets bound north and south, east and west by some primary streets, then print it out and hand-optimize the route.
This literally shows crowdsourcing of updates in action, and makes me want to contribute more where I can.