Try a piece of small diameter tubing (aluminum work good) about half the length of your skirt material. Roll your collar onto the tube, place your skirt material in the tube and then roll the collar off of the tube on the shirt material.
You should be able to just threat the skirt onto the hook just like you are putting on a plastic trailer. Then push the collar/skirt over the collar on the jig.
Put a real light coat of baby oil or worm oil on your hook and skirt collar. It'll slide right over the collar. I use silicone skirts and they don't stick together. I'm not sure how round rubber will react to the oil.
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