I merged your post into an existing similar request … this is also relevant for these ideas, overall: CountyStrides
This needs some thought, but I like the overall idea … something along the lines of:
- click around the map to draw the border that you want (like route builder without the automatic drawing?)
- save it as your own personal area to complete
Gotta figure out the technical issues of gathering streets for a random area and if/how that can be shared (like, others also joining in on the area you created)