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It's really hard to estimate the size of crowds without the help of technology.

Reported crowd size has more to do with if the reporter wants to promote or disparate a group. How they want to “spin” the story.

Depends on how they're reporting on it.

There absolutely are reporters that do this by always saying things like "it feels like... " Etc.

It's however notoriously hard to estimate these numbers and participants generally overestimate the amount by several orders of magnitude.