I noticed today that there are now some drawing tools on the Windows Live Local scratchpad that allow you to draw polygons and lines right onto your map! Cool!
Here's a map that I marked up. Path #1 shows what my "commute" looks like if and when I go to my office (note that by policy, this is not supposed to be mileage that I can expense since it is considered a commute). #2 demonstrates that even after a polygon is added to a map, you can still edit vertices if you need to.
These are groovy features, but one thing that I didn't like was that while drawing the line, there was no way to pan the map. I'm not sure how that problem would be solved since panning normally involves mouse-down dragging, but it is definitely a limitation. (I zoomed out to solve the issue, but this results in a lack of accuracy in placing the points).