I added a lot of parking lots to OpenStreetMap this weekend, but I also added the Willow Creek Community Church (South Barrington, Illinois) parking lots, driveways, buildings, and retention ponds. I’ll let my before and after screenshots show you what I did. Ian Dees, local organizer for Chicagoland OSM data – he has other roles, too – said there’s an application that can generate these images automatically.
I’m also writing a draft tutorial on how to convert GIS data stored as a shapefile to a format you can import into AutoCAD. GRASS will take a .shp and convert it to .dxf (a geo-aware CAD file).