Josh, I agree with you wholeheartedly.  It's very easy to dream you'll throw 
off the lines and not come home for 6 months or more.  Then the day to day 
realities close in, especially if you have a spouse who may like to sail but 
isn't thrilled with the long-term prospects.  Owning a bigger boat has 
certainly resulted in LOT more time, energy and money for the maintenance, 
repairs and dockage.  I strongly recommend folks balance those realities 
against a lower cost, less work daysailer.
Don't get me wrong.  We really love our 37/40+, and down here in the Tampa area 
A/C really is a must, especially if you're going to be on a dock instead of a 
mooring because the vast majority docks are blocked by buildings or adjacent 
large powerboats and don't get much breeze.  However, 2 years into this boat 
and we've really only got out on some local cruising and anchoring a couple 
times, and the rest of the time our old C&C 27MKIII would have sufficed just as 
well with very little maintenance.
Food for thought, 

Bruce Whitmore
1994 C&C 37/40+"Astralis"
(847) 404-5092 (mobile)
bwhitm...@sbcglobal.net
 

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