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Well, I sail a 30-footer, but only liveaboard for the duration of each cruise... When I'm alone, she suits me fine... But when I have company, things can get very tight, very quickly...Here is the other thing. She has asked me if I thing its going to be big enough? Is it too small? I told her is the maintenance and overall cost is a lot better on a 30 foot boat. But I screwed up and Chartered the 36 I down in the BVI this past spring. She thinks that boat was much better in size...
Only you can answer that question, of course - some couples seem to manage just fine on a boat of that size. But in my observation, they are a bit of a rarity out there today, and most more 'mature' couples are on boats considerably larger, at least closer to the mid-30's or so...
I STRONGLY suggest you try an extended shakedown aboard your present boat before making a final decision, or proceeding much further... Trust me, if the size of the boat is likely to be an issue, it won't take long for that problem to surface...
Stuff like a Honda generator will occupy a surprising amount of your storage space on such a boat. Mock up a cardboard box the size of a Honda 2000 (which everyone seems to think is essential these days) and stick it somewhere. Sorry, but you're gonna have to ditch some of those sails. A second mainsail, and that 155 genoa, is gonna eat up much of your precious storage space, as well. That alone is one of the best arguments for headsail furling on a cruising boat of that size. Whenever I remove my sails and stow them below, the space in which to LIVE on board is reduced dramatically...
Other things on your list strike me as perhaps a bit superfluous... I'm a huge proponent of windvanes, for example - but why do you feel you'd need one for "harbor hopping" down the coast, and thru the Bahamas to the Islands? Put your money into a good AP, that alone should be more than sufficient for such a trip...
But seriously, the size issue is the one you must address first, that's likely to be the one that makes, or breaks, such an endeavor...