New Boat w/wo captain...potential charter?

I think you are way off on charter expectations. Not many weekly charters happening in Florida. In Bahamas yes but 70.’ Is very small. Great boats are doing 6-10 weeks a year. Don’t fall into the trap of thinking you will offset costs on this size boat by chartering. Buy want you can afford and enjoy.

Ask again if you'll need a full-time captain or just a captain when you cruise. That may effect your decision on whether to charter or not as you'll be looking for write-offs. On most of the boats I ran I was part of the family and given a SR. On one 65' there was a crew quarters (more a dungeon). Didn't stay with that boat long. On another the owners always got a hotel room for themselves and I got the boat. Once the owner's and I got hotel rooms and left the boat to the guests. You won't find many reasonable crew quarters on less than 70'. Sounds like you'll be spending a lot of time aboard. Add to that down time for maintenance and is it really worth the hassles and expense of setting up and managing a charter operation? No doubt 70' would be more appealing for charter. You might get 4 SRs or 3 + crew which in that case would then accommodate 6 guests. Most smaller than 60' will be 3 SR and one of those might be kid sized. So 4 passenger + crew which increases the cost per passenger for the charterer, again making the smaller boat less appealing . The MAX 6 passenger rule isn't by the insurance company. It's by the law.

Excellent initial post. You have been thinking this through. I see that you suspect 2-3 weeks a year charter is the initial norm and that's good. For now, let's forget the charter possibility.

Crew quarters are potential but the crew quarters on a 50' or so boat aren't something I'd expect any professional captain to spend 12 days on, much less longer. Best to have a stateroom that can be the Captain's. At 70' crew rooms are sometimes ok but still other cabins are better.

You have two very viable options. One is hire a full time captain for the year. If you're boating 10-12 days a month, they'll be busy all the time. Average worker works 22 days a month before time off so take 4 weeks a year plus 8 holidays and you're down to 20 days a month. That leaves 8-10 working days and he'll need many of those to keep the boat in perfect shape if he does things like washing and waxing and cleaning on top of maintaining systems and dealing with issues.

The other option, if you boat less is to hire a yacht management company and then use available captains which they may have or otherwise found for the trips.

Might also be a good time for you to renew/update your license. Go to a school and find out what you'll need to do if interested.

About you needing a captain for a year. I don't buy that. I think it might be nice but I know some insurers will insure after you've adequately demonstrated skills to a knowledgeable captain. I think you very well might be insurable much sooner. Now, I don't know that I'd recommend exploring the Bahamas without a captain as there's so much to learn. There's the waters, the routes, the places, but the people, the resources. Captains can get dockage when you can't or rent you a CC or find a pilot for a marina where one is needed or advise on restaurants and make reservations. For the Bahamas, Captains are also great tour guides. A captain can also teach you all you don't know so find a good teacher. Ideal is even to have them when selecting a boat although don't allow their personal prejudices to unduly influence you.

50' and 70' are equally unappealing for charter. They do some business but no boat introduced to charter will start off great.

Perhaps different definitions of “Captains Licenses”.
In the US it usually means you are a Proffesional Mariner and can take people or cargo out for hire. (You are a paid Captain)

I guess you Captains License from Croatia, at age 16 was some kind of permit to drive a small boat for pleasure?
(Up to 15 meters?)

If I am you with your purchase budget, RTW goals and ten year time line...
I buy the Nordy now, put her in FL, hire a captain if need be as needed, get your two weeks in the sun, cruise FL and The Keys.
Get your Nordhaven all sorted to take off in ten years.
Now you know the boat and are more ready to circumnavigate the globe.
The only catch I see in this plan is that you want a $2MM Nordhaven as your eventual boat.
I would not charter my boat. I would not buy a boat that chartering be required to keep her afloat and maintained and ship shape.

12 pax requires certification. So you're not going to do that legally with most boats in that size range. Most of those I've known who charter in that range are liveaboards looking to write off some expenses, not make profit, and that can open issues with the IRS. One other thing to consider is that "Fish and house guests tend to stink after about 3 days" and that's the best of them. One wrong guest, a few rainy days or a sea sick guest and the For Sale sign will go up on the aft deck. If you want to charter stick with day charters. Much easier to plan, cancel, provision and keep track of expenses for, and at the end of the day the guests go home. If it were a money matter I'd do a fractional ownership situation before chartering. Like having the whole year's charters booked. no passenger # restrictions and easier bookkeeping.

Legal bareboats can carry whatever the boat's capacity is...if you dare. It's their boat. But as you've pointed out before, they're cracking down on pretend bareboat charters. I'm not suggesting any charter, just giving the OP options.

Correct. Is that new?

I never looked that up before, no need, but a bareboat charter is basically their boat so I'm surprised. Think that's followed at Haulover? I know it's not in Lake Havasu. You added to my education. Thanks.

I don't even like staying at B&Bs cause I feel like I'm in a stranger's home, guarded. So I definitely wouldn't be one to charter a small boat except maybe bareboat. I think a lot of people would feel that way. So it's definitely a limited market. Good luck. Sounds like you have an exciting spring coming.