>and if possible, how does inertia play (or not play) a part in this?
The air inside of a train is moving at the speed of the train.
The air outside of a train is not moving at the speed of the train.
A person standing on top of a train is experiencing wind according to the speed at which the train is moving – and all forces associated with that. A person inside the train is not experiencing any wind.
This is caused by the inertia of the air. It resists being moved by the train/person pushing through it.
Jumping on top of a train within a vacuum would yield that same result as jumping inside that train.
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