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I covered the tops of the stands and the top of the bottle jack with several thick layers of Plasti-Dip so they won't tear up the paint on the trailer.
Great idea. Not only does it protect, but it's probably safer as well assuming the Plasti-Dip doesn't gel in high temps. I used to work for a house mover while I was in college. Not furniture movers, we moved whole houses. Also, no it wasn't the guy in Iowa who had a TV show a year or two ago. Anyway, the first two rules learned on day 1 is:
1) Never get under anything that is solely supported by a crane, hoist, jack or any other mechanical device. Mechanical devices can and do fail, and you don't want to be under anything when that happens.
2) Metal on metal is slippery and can slide. It doesn't take much to add enough friction to limit the potential of a metal surface from falling off the jack. I simple piece of 1/4" plywood will help a bunch. I always keep a small piece of plywood in my truck toolbox just for this type of purpose. Also, the paint on the trailer will help some, but as you eluded to, it will eventually where off if you jack on the same spot each time.
I know the risk is even more so limited on a tandem trailer with the wheels blocked and/or hooked up to tow vehicle with parking brake on. Still, those two rules stick with me and I refer back to them everytime I raise anything up with a jack or hoist.