Density estimates can be tricky, though, and crowd densities are often not uniform. Area estimations can be a good starting point, though, certainly.
I agree, but there are some minimums that cannot be breached reasonably. The average person is about two feet across the shoulders and requires about 10 -14 inches front to back and so requires a minimum of two square feet, even in a dense crowd.
If the Media are claiming 70,000 showed up in Portland, and the area is definitively measurable as under 50,000 square feet, you know they are lying.