This was a wonderful post, thanks for the honesty and detail, emacsen. What I'd like to see as far as a technical overhaul, is reimagining the entire thing as

This was a wonderful post, thanks for the honesty and detail, emacsen. What I'd like to see as far as a technical overhaul, is reimagining the entire thing as a 3D dataset. Needing to model a paper map is no longer the goal, modeling space in 3 dimentions seems to be the more exciting/useful way forward. I'd like to have a model of my town in 3D, either at mostly manual low-poly resolution (aka minecraft) thats done by hand, or (though much more data intensive) with point cloud/lidar data. Web pages can receive the 3d data and render a 2d model, or the server can project 3d onto 2d tiles before delivery.