Requirement to be licensed?

The insurance company will base their assessment on the work that was done. It's as if the owner herself had done it. He can tell them about his experience, and explain his recommendations, but have him make it crystal clear that he does not hold a Master's or any other relevant license. I wouldn't lie or even give a false impression to someone's insurance company. I wouldn't expect that there can be much of an increase in value on a 20 y.o. 25' boat. Sounds like an insurance broker reading off the questions he's supposed to ask, but the answers would be more important on a 50' or 80' boat.

As long as nobody pays to be on the boat, a license is not required and for such a small boat, the underwriters should not require it since he s just a caretaker.

As to a license, or even years of experience, being guarantee of safe operations... We see that theory at work every day on the roads, don't we? And at least drivers are required to take a road test!

USCG license experience requirements are a joke... Being a mate on a boat for years most of the time will not qualify someone to be a captain and makes the decisions that go with the job. I ll even argue that a guy who takes a tour boat round the harbor or a smaller Sportfish charter out for years may not even be qualified to take a high draft boat thru new routes, inlets and harbors despite years at the helm, grey hair and multiple issues.

I have seen very experienced captains finding themselves completely out of their depths, literally, in a new to them environment

All true, but a license at least guarantees some sea time. There are a lot of people who would go from never being on a boat to buying a tour boat if they could. I'm always amazed by how many people ask if you have a license, but never ask the follow-up questions (What issue are you on or what kind of experience do you have). I once took a 50GT Master on as a mate for a trip south. He got his sea time from owning a 26' runabout. Every night he was drunk, every day he was green. He fell asleep at the helm with me sitting right behind him, would have run over a diver another time if I wasn't there, and tried to run up the stern of a boat dragging baits.
I would never turn a boat over to a captain who wasn't on at least his 2nd or 3rd issue. Experience is far more important than the license.

I respect those with lots of experience but I also respect those who compliment this experience with licensing. I do intend to use licensed captains as well as get any crew properly trained in the areas relevant to their jobs. My wife and I also both intend to get our licensing. We will go through the school training and meanwhile start building up hours of experience. That will take us considerable time. Our captains are very good at training and we're appreciative of that. Our goal is to get our 100gt Masters Near Coastal as soon as possible. That means we need 360 days over 34gt. We will get 50gt first as we'll get to the 180 days over 5gt and 360 offshore quicker. Like many getting started we have tons of inland experience. At this point we now have 30 days each of offshore although it's all between Beaufort NC and Key West so far. Once we get a larger boat then we anticipate reaching the goals in 18 months. So hopefully we'll be 100gt Masters Near Coastal in two years. 200gt for us is probably four years away. 500gt would seem possible in 5 to 6 years.

We take it seriously and to do otherwise we feel would disrespect those who have worked hard to get their licensing. We also intend to take extra courses that aren't direct requirements but we think could be appropriate for our plans. None of this is designed ever to rid ourselves of professional captains but to just make us more able to Pilot and Navigate a vessel as well.

If your son is running their 25' boat around and getting paid for it, he legally needs to be licensed with a OUPV Coast Guard License at the minimum. If he just drives the boat for them and is not getting paid to do so, he does not need to be licensed. If this is the case, the owners of the 25' can list him on their insurance as "additionally insured" and he would be covered if he was driving their boat. He could work out some sort of monthly fee for maintaining the boat, and run the boat for free for them when they want to go out and that would be legal.

Sorry captJ, but you are wrong. He doesn't need to be licensed to get paid for running a private boat. He needs to be licensed to take passengers for hire (there's a difference), or to do most commercial work. In fact I intend to let my license lapse, but I'll still be running people's boats. The only one's that may grumble are insurance companies.
It's the same as on land. Your neighbor can pay you to drive them places in their car, but if you have a car and want to hire out or work for a company that hires out you need a Chaufer's license.