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Interesting theory, but I don't think a stationary shooter and moving spotter is likely. I was in the area last week. Georgia and Connecticut Ave as I remember are busy four lane roads, two in each direction separated by a median, but not limited access highways. There are mostly, as I remember 1-3 story businesses like gas stations, small strip malls with things like a dry cleaner and Subway etc in most of those areas.
The cross streets are two lanes I'd guess with a mix of residential and small businesses.
I don't think you could get line of sight to each spot unless there is some tower or anntenna I did not notice and I also think the shooting were too far apart for a 223 anyway, although this all did happen in a fairly small area.
The traffic on the north south roads was pretty busy at 7-10 am when I was driving in the area. There was constant quickly moving traffic on those roads. There are also traffic lights every couple of blocks as I remember.
It seemed like a mostly nice middle class suburban area, lots of neighborhoods off those side roads of 60s era smaller suburban homes. I think the area gets nicer/more upscale as you move farther north of 495.
There is a big retirement community, I think called Leisure World, on ???? one of the two main roads in or near Aspen hill that might be a little bit taller building.