In my experience, when you're on the water, the wind tends to string the chute out a bit and it doesn't wad up as much. When I have issues on shore its usually the wadding-up problem. I'ts also usually either calm or the breeze is on the nose of the boat which are not ideal either.

You might try turning the boat so the wind is coming across the beam. This is probably a closer approximation of your apparent wind when doing a take-down on the water.