Back to the insurance bit on trailers...
My insurance - state farm - does not cover a trailer because it was attached to one of my vehicles. In fact the language in my policy specifically mentions this.
The trailer itself has a policy attached to it which covers it no matter who is pulling it. It's cheap but required. This is separate from policies that cover what is being hauled. IF I were to yard sale my boat on the road, the boat policy picks up some and the trailer some. Between the two any damages and liability would be covered up to whatever your cap is. In this case my auto coverage would not be touched unless the tow vehicle were somehow also damaged. They also pointed out to me that I need to be aware of the coverage or lack thereof if I hook up anyone else's trailer which would not be covered by them should anything happen. I suppose thinking about it - makes sense they don't want to take on unfunded liabilities.
Far as U-Haul goes or any other rental trailer, they are not covered under your policy - that is why they offer to sell you coverage if you rent one. If you look on their web site (I did was curious) they even say rental equipment is not typically covered under a car policy.
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