This was a very interesting thread for me. Love that this forum can surprise like this.
Now, an honest question.
I would have the same reservations as the OP -- new, or new-to-me boat... likely bigger than anything else I've owned.... long trip over unfamiliar water... hiring someone to get my boat safely to her home port sounds like a reasonable response.
But if a hired delivery captain, at the helm, runs a boat aground... He apparently has every legal right to simply walk away? Well then what good is hiring that captain?
Should I (we) simply take our chances and make a best effort on our own delivery? Because if we run aground -- well, it's the same yard bill, but you've still saved the captain's fee...
You hire a plumber or a HVAC person, or you take your car for repairs, or many other things we all do regularly and the service isn't right. Plumber leaves a mess after charging $600 and now you have to get another plumber who points out the things the first did wrong. Does the first plumber just walk away?
Well, you can report to Better Business Bureau or post reviews on Yelp or Google. But are you likely to ever see the $600 again or even part of it? No. Are you going to sue? Get another plumber to testify?
Many times when our choices don't turn out to be the right person, we have no reasonable recourse that doesn't just add to our misery. I've never sued, never been sued, hope to never do either. The lessons I've learned are to be much more selective and careful up front. Deal with those I know do good work, but also I know respond appropriately to problems and complaints.
One of the key factors here than slipped by a bit was the OP pointed out later that there were other problems with this captain along the way. That changes my thoughts, that it wasn't perhaps a good captain making a bad mistake but a not so good captain making another mistake. To his credit, the OP recognizes some things he could have done better himself. But ultimately, because the OP has shown himself to be fair and balanced, I suspect his selection of Captain wasn't the best.
Half the captains out there are below average. Just like all professions. I want my doctor and my lawyer in the top group, not the bottom. Selfish that way, someone else can take the bad ones. Same with Captains.
There are many professional delivery captains who do it regularly and have extensive lists of references. They deliver for builders. They deliver for brokers. They have businesses, fully credentialed. But there are also captains who deliver because they don't have jobs or other work. Do it, not by choice, but at cut rates often due to their lack of good reputations. I know quite a few captains very well. Most, even of those who do boat management rather than being assigned to a yacht, wouldn't have time for this delivery.
One other thing I'd point out. Many delivery captains will not do it with owners or others aboard. They'll bring their own crew if needed. They'll do long runs to get there as quickly as possible. I wouldn't use one of them probably, too obsessive over keeping an eye on things. But I'd probably use a regular captain and do it as a trip. That would cost significantly more too.
But ultimately people often do bad jobs and bad work and we end up stuck with the cost of it. Some industries have horrible reputations and I feel for the good ones in those industries. Look at the service records of big box computer stores or of moving companies. Look at products like Nuwave being sold by the ton on infomercials and elderly women shocked when the $99 plus all the freebies end up costing $260 by the time they reach her. Look at the scams run daily which are far worse than just bad performance.
But seldom does the legal system work well for resolving these unless you end up on People's Court, Judge Mathis, or Judge Judy and get an appearance pool from which the winner is paid. Even small claims which is the best of the system isn't so great for most people who work. Let's see, filing fee, time to go file. Then take a day off from work to go to court. Then, if you win, try to perfect the judgement and try to collect after they don't pay. More costs. And right as you're catching up to them, they file bankruptcy and now you're tossed in the pool of people not getting their money.
Arbitration is written into many contracts as the means of resolving a dispute but that by no means comes free either.
The biggest protection other than good selection that we have is not to pay until after performance. But when it's work on your home or your car or your boat withholding payment gets dangerous too. For instance, the worst auto repair shops are always the best in terms of getting you to sign contracts giving them liens and always very expert and experienced in enforcing those liens. They know the system and use it effectively.
I do believe in well written contracts, and the use of lawyers for them, although I do instruct my lawyers not to turn it into a major project but just address the major issues. However, the contract only really gives you legal standing. It doesn't keep bad service from happening and it won't make up for that.