I've done tons of skirts in chairs simulations. It's not too hard. Things to remember. Have the figure and the chair far enough apart that the skirt isn't intersecting the chair. Make sure the figure isn't intersecting the chair when sitting. You don't need to have the chair move to the figure after the figure is in a sitting position. You can do them at the same time. Set the collision offset and collision depth between the chair and skirt low, like at .1 so it doesn't get caught.

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