Interesting question. In 27 years of boat ownership, I've never been asked the question and it's given me pause.
SailNet is full of what-if's, required skills, and casualties. So those with what I consider the requisite skill set to safely and effectively operate a boat of our size and complexity, are very few. Like two people. Who already have their own boats. And don't need mine.
Will it break me to lose the boat? No.
Do I trust my boating friends? Just two. I'm a good judge of character too.
Do I have a good attorney? No. Don't need one but know where they are.
Do I trust friends to compensate me if something goes wrong? No. Prudence tells me not to trust when dealing with money. I assume that I'm in it alone.
Would I be torqued if something happened to my boat (and it was the friend's fault)? Oh yeah.
Is it just a thing? Yup, but it's my thing and I take care of my things (as my parents taught me).
If you want to go sailing, I'll gladly, gleefully, willingly take you. If you want to go without me, charter your own boat or buy one.