I get a lot of email in the vein of "what is the perfect boat to cruise/build/buy" and most of the time I get the distinct feeling that the folks asking are disappointed with my answer... So to save some folks time and effort here is the stuff they don't want to hear!
There is no perfect boat!
Not only is there no such thing as a perfect boat but you cannot make an imperfect boat a perfect one by pouring money into it. As no matter how much you pour in, it will still be a boat.
Money does not work!
Neither will the new flavor of the month gee-whiz-flash-bang new technology make your boat a thing of perfection... Sure it's fun to keep an eye on the cutting edge of high tech but adopting it willy-nilly will just give you high tech problems...
Avoid High Tech!
No one type of boat will be easier to sail and design is no substitute for actually learning how to sail. Sailing is easy and most folks can learn all the needful stuff in a weekend! That said, no matter how long or how far you sail, you should keep learning as there is no end to the learning curve on boats... Learning is GOOD!
Learn to sail
Bigger is not better or more seaworthy but it is certainly more expensive. Over a certain size threshold, if you are dealing with forces where you need "help" to do basic things that is a way a boat tells you it is too big for you.
Smaller is better
Building your own boat is not so easy. It takes time, money, and more than likely you can spend less and have a much better boat by going the Classic Plastic route. Classic Plastic is also the most eco-friendly way of getting to sea as it is reusing resources and in my mind that is something of a slam dunk. So, unless you really need something really specialized or love the actual craft of boat-building, you should seriously consider Classic Plastic...
Classic Plastic Makes sense!
Way back when we decided to retire and go cruising with Loose Moose 2, the fact that made us decide to go then rather than wait till we had the perfect bank account, the perfect boat and all of the stars in the sky were aligned perfectly was this...
We had joined the SSCA and while reading each issue filled with people having wonderful adventures in faraway places, we noticed a certain constant in the obituary section of the newsletter of people who had waited till they had the big boat, the right amount of money, the kids all through school, and all of their various stars in the sky aligned just right only to have a heart attack or stroke at the beginning of the long planned dream cruise. Seriously big bummer that...
Life is far shorter than most of us would like and if there is a certain thing you dream of doing ... Well, the phrase that comes to mind is "Get to doing"
Just do it!