How: Determine area painted by a path with width within a polygon

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I have a path that represents the movement of some equipment. The equipment has a width so I'd like to determine the approximate area created by this path within a polygon. If I use the distance between two points to determine the length of my fill rectangle and use the equipments width for the other sides I can get an area filled in by my path.

However I am at a loss on what I could do to determine overlap of the path or partial overlap of the rectangles between points.