I really doubt a homeowners policy would take care of normal wear and tear or even abuse to a power equipment. Stolen is much different.
Groups of people are different loan-wise. Some loan and borrow at the drop of a hat and everything works out well for them untill they get burned good. My parents and uncles worked that way for years and it seemed to work. Of course the one with the equipment was everybodies best friend.
I have noticed that the people who "generally" want to borrow things are busy spending their money on "fun" things.
My brother for example wants to use my log-splitter, cement mixer, tractor and whatever else, but he is sitting there with a new super-glide in the garage and 3 new 750cc 4 wheelers. Not the cheap ones either. It's not hard for them to rip off a couple thousand bucks for a stockpile of guns just for the sake of collecting them. They just don't want to part with their money for those things. He just put in an outdoor wood-burner and now he is going around trying to borrow and doing a good job of it, trailers, skid-steers, log-splitters ans so on. If you need one and will in the future, just buy or rent.
Also, it would not seem fair to loan out some motorized equipment and then have them start it up and through no fault of theirs, it just breaks. You could definitely lose a good friend if they are expected to fork out $500 to fix something when it was just its time to go. The same logic would be if I would borrow an expensive piece of equipment and started it up and it broke. I would hate to fix it.
I agree with many other posts that if something has to be done, the operator goes along with the tool. Especially if is worth more than a few dollars. If I go along and it breaks, then no one can complain, especially me.