I'll add some opinions or actually some things to consider, but remember that you need to feel comfortable with what 'you guys' feel is safe and smart.
First, have you been out with the boat at least a month at a time, preferably at least 2 months at least once? That will tell you a lot about if the boat is going to be what you want for extended cruising. If you haven't done the above and still want to keep the boat I would sure suggest you do it and at the same time maybe run down to Oregon and back and see how you still feel after that.
A lot of the replies you have received deal with the Caribbean. I'm wondering what is the draft on your boat. Looking at specs it looks like it comes with a couple different draft options. If it is over 5 feet and you want to spend time in the Bahamas that probably wouldn't be an ideal draft there.
Next is getting to the Caribbean in the first place. You aren't crossing from Florida. You are a long ways from there and you could probably expect to face a lot of different situations getting there. Once you leave the coast of California you have a lot of ocean down to the canal and from there east plus getting from where you are to southern CA is a trip in itself. If there are just two of you aboard this could be pretty strenuous. For sure others do this all of the time, but for instance Ruth and I couldn't handle long off-shore trips at our age very easily. If we did them we would want to be in a boat that has a lot of safety built into the design and not just count on our skills entirely or hitting perfect weather windows. It sounds like from your post you might have some concerns yourself about the boat making such a journey. And then there is the return journey unless that isn't planned. Going north on the Pacific Coast is even going to be a harder trip.
We have a frig even on our small Mac and I'm building one now for the Endeavour. We wouldn't want to live without it. If you plan on the same you need power. You can run a generator or the boats diesel everyday for that or add wind or solar. If Solar I feel you need a minimum of 300 watts and 400 or more would be better for the needs of other items other than the frig and that is being real conservative on the 'other items'. If you are going Solar do you have the room to mount enough panels on the boat?
Has the standing rigging ever been replaced on the boat? I'd for sure want to do that before a trip like you are thinking about. How about the rest of the boats systems, like thru-hulls and tanks and such? How about the boats anchoring gear. I'd want at least 2 anchors and rodes that are sized for a 35-45 foot boat considering the trip you are planning.
The reason I mention the above, besides safety, is that you could end up spending a considerable sum on the above to get the boat ready and in a safe condition for what you have planned. We put thousands into our Mac and now are doing the same with the Endeavour that we will never get back when we sell them. For us it is esential though to our safety and so that we can enjoy long trips on both boats. Right now to add just a frig and about 500 watts of solar to the Endeavor we are spending over $1500 for panels, wiring, charge controller and a mount to locate the panels and then the frig is coming in around $1000 and this is with me doing all of the work.
So if you put a pile of money into your current boat to make it safe and somewhat comfortable and it doesn't work out where are you then? Maybe think about what a couple of the other guys said above and put that money into a somewhat larger boat. One where a number of them have made voyages like what you want to do. This is basically what we did when we bought the Endeavour. I wanted the safest boat I could find for Ruth's sake that would be a good boat for the waters we wanted to cruise and would work with our budget. Of course it isn't the only one that would of meet our needs and there are a number of boats out there that I think would also meet your needs maybe better than what you have now.
I'm not saying the boat can't do it, but I wouldn't feel good about taking the voyage you are talking about in a boat that displaces about 9,000 llbs. and has 3,000 lbs. of ballast.
The best of luck,
Sum
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