Step kids, in laws, old friends...these can be the worst situations.
Not everyone thinks of issues beforehand that could have prevented arguments or issues after the fact, and not everyone is good at saying no.
God bless your insurance man.
My 85 year old father just bought a brand new 10k John Deere tractor as part of his bucket list. My wife and her oldest brother are no problem when it comes to using their dad's stuff; the youngest son not so much.
Just borrowed the tractor and brought it back covered in mud, brush and scratched. Not a word, just parked it and left. My father in law will stew, steam and gripe to everyone but his son, and then loan it to him again.