"But don't make getting liability insurance any kind of priority."
All well and good to compare philospphies of life but that wasn't the OP's question.
Let's suppose one of you top experts hits a deadhead at night, stuffs a foot wide hole in the hull and loses a cheap quarter million dollar 40'er. The owner is a nice guy but his wife is really pissed at you and files suit, saying it was irresponsible of you to sail at night when you couldn't see what was out there. She gets a jury to agree and you get screwed. Hey, sure, you did everything right and **** happens, but that also includes courts making the wrong decisions and now you're being held liable for a quarter million dollars, and also the loss of her prize winning pomeritzu dogs who last were seen going down with the boat. They were prize-winning breed stock and gifts from Leona Helmsley, valued at another hundred grand for the pair.
You're screwed. You will now lose 350,000 dollars, from your house, your retirement funds (they're not all inviolate), your own boat, whatever you've got. It doesn't matter how good or professional you were, folks get caught up in this stuff all the time and SOME folks would really rather just buy insurance than risk the loss.
It has nothing to do with how qualified you are, how responsible you are, how experienced you are. It has to deal solely with how you chose to ensure against risk of loss.
Solo delivery captains may be the last cowboys, riding off with just a horse and saddle. Much of the rest of the world? Isn't quite so brave.
You're absolutely correct, of course, and there is certainly a good case to be made for carrying liability insurance... My response was simply more to the general tone of Andrew's musings, rather than to the OP's query (who seems to be getting a bit ahead of himself in certain respects, by thinking of purchasing a life raft before owning a boat, for example (grin))
I've always viewed the delivery business as a surprisingly 'intimate' one, as you're assuming command of a possession that is very dear to most clients... Personally, I cannot imagine having my own boat delivered by anyone else, and there has to be an extraordinary amount of trust involved, on the part of both parties... I've been lucky, since deliveries have never represented my sole source of income, I've usually had the luxury to pass on deals that didn't 'feel right', or that I sensed might turn into a real PITA... As with most any profession, one develops the ability to sense the likelihood of a particular client being one that might best be avoided within the first minute of a phone conversation... One of the first things I learned getting started out, is to always go with my gut feeling in that respect...
Obviously, guys like Andrew and I are still operating by modes of 'responsible behavior' that no longer apply... We've both gotten away with it for decades, but I'm sure it's just a matter of time before I sink some client's million dollar baby, his own insurance refuses to cover the loss, and he turns to me for payback...
One thing I do have going for me that might help me avoid your scenario, however:
I would never, EVER run a boat with a pair of prize-winning Pomeritzus along for the ride... (grin)