If I understand correctly what you're trying to do, here's what I do:
maps.google.com
Select Satellite view
enter first location and mark
enter second location
right-click on either location, and select "Measure Distance"
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Click on your second location
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This will give you the distance and then what I do, is zoom to look at for obstructions.
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Like I said, I'm not sure if this is what you're trying to do, but this is what I do.
Hope this helps.