Having seen many dream and few complete I would suggest taking a two to four month sabbaticle from your current jobs and trying it out first.
Many dream, but very few take a test drive. They then they find they don't like the vehicle because they never test drove it... Bay sailing on weekends or for two week vacations is VERY, VERY different than 24/7 with four people on the same boat no matter how big and is NOT a real world test drive.
I've seen more folks deck out a boat over a three year period only to be back in three months wishing they never sold the house and then they eat thousands of dollars in non-recoverable losses due to the upgrades they put into their boat that they never recoup. S/V Flight of Years is a recent example of this..
Dreams are nice but the realities of a 24/7 three or four month test sail will confirm if you're ready, wiling and able..
Just my .02
-Maine Sail / CS-36T
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Last edited by Maine Sail; 02-11-2008 at 10:23 AM.