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Depending on the position of your character and the amount of movement, it may be easier to add the shadow in the closer shot than remove it in the wider shot.
But you have other problems. The overall light intensity is quite different between the two angles, so you'll need to do some clever grading to try and match them. And the red-shirt guy has quite different shadows on his body due to the change in sun position. There's not much at all you can do to fix that.
Ok adding the shadow works best anyways. The shots are still so no motion tracking is necessary. Now, is there an easy way to apply the effect even though the actors arms are crossing through the shadow frequently?
Tht's where rotocoping comes in. You're going to have to mask the arm movement frame by frame. There's not enough contrast between the arm colour and the background colour to do a key or auto-trace. It has to be done by hand.