Can I spray the plug with silicone spray to make it easier to do? Or is there something specifically designed for this that is conductive and won't gunk it up? I don't like the way I have to wiggle it to get it out everyday. Even though I grasp it by the plug and not the cord I don't want to be putting any extra tension on the wire.
No silicon! It can mess up electrical connections. Try a different extension cord that has a looser fit. JeffD
I had the same problem. I think the stickiness lead to the eventual failure of the EBH cord. My solution was to mount a waterproof plug in the bumper and get a new end for my extension cord. So far I have had no problems with my setup and the power cord slips on and off of the plug very easily. http://priuschat.com/forums/prius-modifications/45043-hidden-ebh-plug.html
Get some dielectric grease at your hardware store. Not sure of the spelling, but that's how you pronounce it. It works great. The Milwaukee Hybrid Group people were pre-greasing all their new installs last fall.