Hey Bryan,
...I think the overwhelming percentage of people would be more successful if they do what myself and many others are doing nowadays - namely, doing the longer or more arduous passages by themselves, or with a crew that enjoys that sort of thing, and then having their significant others join them when they reach those exotic destinations, where they can revert to a form of coastal cruising...
Of course, this style would exclude most families, and for the majority of us would necessitate cruising in much more modest boats, as the selling of the home to trade up for the full-size globe girdler might not be an option...
One of the happiest cruisers I know of right now is an occasional poster here, John Reid on RAMBLE... He's about a week out of the Canaries now, on his way back to the islands, I've lost count of how many times he's gone back and forth across the Atlantic in the last few years... His wife still holds down the fort back in Vermont, joins him in places like Greece and the Caribbean, an arrangement that works beautifully for both of them... As beautiful as RAMBLE is, she is relatively modest and cramped by today's standards, but she sails like a dream, and he's got his priorities straight...
For those who haven't seen it, John's blog is one of the more pleasurable reads out there, this guy knows how to cruise, or at least what works well for him and his family:
http://svramble.wordpress.com/
IMHO, much of the problem today is that cruisers now appear to "Want it All", in much the same fashion that a generation of "liberated" women a couple of decades ago began to buy into the notion that they could have it all, an easy balance of career and family that would be as simple to maintain as the latest $2 million cruising boat from Lyman-Morse... Americans as a whole have long ago forgotten that the origins of the word "travel" arise from the word "travail", and most still want to avoid inconvenience or discomfort above all else, and can't seem to understand why cruising can be no different from RV-ing, with all the comforts of home...
Cruising is all about trade-offs and compromises in virtually every choice or decision you make, just way too many people out there now who refuse to accept or adapt to that reality.... doesn't fit The Dream, after all... (grin)
best regards,
Jon