What qualification is recommended ?

A captain's license with the highest tonnage your seatime will allow.

For USA authorities you need nothing. Ins will demand experience on similar vessel but don't really care much about a lic.

Most companies will give a discount if the owner has a license, or they'll let an owner jump a little further (length) between boats if the owner has say a 100 ton master......normally might only allow 45'-55' and with a 100 ton they may let an owner go from 45'-65'.

How does the length jump work with the insurance companies? 10ft is what I heard.

I jumped from 35 to 62 and ins required captain for 4 months until they signed off. Which was a good deal on all fronts.

Usually 10' but it depends on owner. An owner holding a Captain's license goes a long way to make the jump a little further in between. It really depends on the insurance company, the owners resume, and many other factors. Having a Captain train you for a period of time also helps like in other posters situations.

I went from 33' to 60' and the only thing the ins company required was a checkride with a licensed captain, then for him to sign off acknowledging that I new how to manage the boat, knew about navigation, etc. That was all done in an afternoon.

The Op will be doing some hard core cruising, so a license may make sense for reasons noted.

However, for the typical recreational boater, myself included, I don't think the liability aspects that come along with the license make sense.

This has been covered ad nauseum on other forums, and I realize it's a personal decision. personally, I wouldn't do it.

This subject has been discussed on this forum as well. From what I gather, there is no increased liability by having a license. Only good things such as discount on insurance, ability to jump to a much larger vessel with the blessing of your insurance company, ability to charter for pay, etc. Can you elaborate as to the increase in liability about which you are referring? Many thanks in advance.

Nycap was the strong proponent of that argument. I never bought it and have never seen any evidence it's true.

I've never heard any evidence either

When I took the Captains course, the teacher there taught that the licensed Captain had a responsibility to " Take over" if the owner/operator was not operating the boat correctly.

That's pretty subjective, number one and number two, as I think it was pointed out here, that could be piracy !!

I think the increased liability is if the owner/Captain is drinking or there are drugs on the boat, illegal activity sort of thing. I also think the USCG would hold a licensed Captain to a higher standard if there was an accident. But again, I haven't really seen proof of it. I also think it's a good idea for an owner to get his USCG license.

I agree with CaptJ, especially since incidents involving injury or property damage subject the licensed personnel involved in the operation of the vessel to an immediate alcohol test and a blood test at the first opportunity. It bears noting that licensed personnel are presumed intoxicated at 0.04%, and non-licensed are subject to the standard of the state's waters. That could impact the enjoyment of a day on the water for many operators. According to the BA chart supplied by the DMV, it doesn't take much to hit the 0.04% level.

Actually, yes I have heard of situations where the licensed person was held to a higher standard in court after an incident.
Do I have proof, or a specific case to reference? No, just personal accounts from others on websites - anecdotal, so I take it for what it is worth.
I once held an unlimited HP/Tonnage license, but that was 30 years ago so I am familiar with the process.
Now I drive a 44 ft. boat around on the weekend, and longer in the summer when I can get away from work.
I stay on top of the rules, practice good seamanship, and come on forums like this periodically to learn from others.
To each his own, personal decision imo.

Nope, I actually leave that category to another group of folks, and the middle red states. Point being, web forum info can be fairly good, but also worth what you pay for it. 0. I always find the web stuff interesting. If someone one doesn't like another's point of view, its fall back to an insult, passive aggressive included. Fletcher out.