The skipper is the key
I absolutely agee with J. It is the skipper that counts. Consider Robin Lee Graham. He sailed a relatively light displacement monohull named "Dove", a Lapworth 24, early kin to a Cal. He made 3/4 of the way around the world before the boat gave out. Regardless, he didn't sink! He, the prudent skipper, recognized his dillemna and got a new boat to finish the trip (Allied 33, I believe). As for me, I went throught this excercise over the last 6 months in earnest. I have decided to get out of the armchair and local coastal sailing and buy, God forbid, a beautiful Hunter 356 or nearly new 380 with creature comforts to boot. I will try to be ready for the 2004 Singlehanded TRanspac out of SF to Hanalei Bay HI. I'll return directly before the Pacific High loses its stability and cover close to 5000 miles in 2 months. Am I crazy? Maybe, but again, I believe it is a prudent skipper that makes all the difference. Focus as J said on yourself, your piloting, your navigational, your mechanical capability, your diesel repair etc, etc. Buy the best boat you can afford and just get out there. LIfe is too short, and we do sit by and watch our chances pass us by sometimes. Go for it!