RE: Insurance issues on riding someone else's bike, or them riding yours
Much of this is going to depend on how your state insures vehicles. When I was in Wisconsin, insurance is on the driver, thus anything that I drove was covered by my insurance policy. If I wrecked someone else's ride then my insurance would pay and have the point applied to it.
Now that I am in Minnesota (damn I should go somewhere warmer) insurance is on the vehicle with a designated primary driver. Thus if my buddy wrecks my bike, the vehicle insurance pays, thus it is my insurance, and the claim would stay on my insurance's record.
I have no clue what the NY rules are. Hope this helps a bit.
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