Tailored for Virginia, using Virginia data.
Probably the easiest way to start is by using the Rapid editor. This assumes you know how to use the Rapid editor. You can save yourself a URL with a few custom parameters to open the editor.
background=VBMPImagery_Most_Recent
datasets=msBuildings
map=10.37/38.1811/-79.1423
This updates in the URL as you scroll and zoom. So just navigate the map to your favorite spot, and copy/paste.
poweruser=true
Allows one to make large edits (>100), and use preview datasets.
Simple Task Manager works well for organizing and tracking your work. It tracks only by area, not by mapped feature like Map Roulette.