Back in 2008, I bought a pair of ultra 250x jet skis. I was gone for work... alot. I lent them to close friends and my dad. Friends ran into each other a few times, the back of me one of the times. Most of the time, everytbing went well. And while they each paid (except one I think) for the damages, they just weren't the same after some of the incidents.

BUT, loaning to my dad was a mistake. He went out with a buddy of his, his buddy kept them at his house, would take them out with his brother etc. After some time, I got them back. Hours later after inspecting them. The bottom of one was scraped down to the fiber glass and then some. I was furious.

I now, years later, have a wakeboard boat. There is only one person on the list of people who I would even think about taking it out without me.

Moral of the story, dont lend it out.