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Congrads- A lot to think about and arrange. I'm "walking the plank in 90d. Took all of 2yrs. to get everything arranged and still at it. Don't know your business or background but for me/wife it was hard disengaging from various land responsibilities. Make time to sit with your accountant, financial advisor, and family. Lay out your plans. That way you can see what work you need to do before you leave and have a rough idea of the budget you are working with before you look at boats. Its a shame to see people home bound because they are house broke or cruisers stuck in one place being boat broke. We ended up doing wills, trusts etc. before leaving and assigning agents etc. in our absence. Also need to think through selling/storing assets. We decided to hang on to the house for at least 3yrs. as a fall back. Then need to think about leave it empty or rent it etc.
Turned out the boat was the easy part. Wish there was a check list but everyone's life and family responsibilities are different.
As regards the boat for us knew this would be our last boat and our home. After several years of crawling around hundreds of yards, talking with a zillion people, going to innumerable boat shows decided to build a semi custom from scratch. Others decide to get a used vessel which also makes great sense in the current market. However, if you do so remember this is different than day sailing or short coastal cruises. This is you life and your house so leave an extra 20-30% of purchase in the kitty for refits and updates. Read all you can about what's needed for safety and to be a self sufficient cruiser. I had no real idea of the extra spares/tools is smart to carry once you spit up the hook.
Know everyone is different but need to think if your new boat can be run single handed by either one of you assuming you want to sleep time to time. At first thought 46' was large now see I was given good advise by other cruisers saying 40-50' is a good size for a mom and pop boat.
J+B make nice boats but agree they were designed with another purpose in mind from what it sounds like you want to do.
 

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May want to read the catamaran thread. Personally wanted a boat that would take care of me passively in a storm and although I could afford the purchase I could not afford the up keep a cat big enough to do blue water would demand.two engines, more yard fees for hauling, storage etc. more to heat or cool. Wife/ I decided a spare stateroom with its own head and 7 sea berths was enough.
You're heading to the Caribbean. So are we this fall. Stay in touch and send a pm when you get there. Great for our learning curve has been to help friends with transports. Not as much fun as cruising but get to learn the mechanics and logistics of moving boats around country to country.
 

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That's why I suggested meeting with your professionals first. Taxes insurance permits etc. are going to influence your decisions. For us we saved a bunch on taxes after accountant ran through options on how to buy the boat but did it very conservatively so wont be problem in the future. As with everything look before you leap.
If I was where you are would be looking at Malo, Hallberg Rassy, Rustler Boreal and the like.Spend this season trying to sail as many different boats as possible while getting your ducks lined up. Would bareboat in turkey or the like for a week with your honey. Be in a position to make more informed decisions.
 
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