Having moved up from a 27 MKIII to a 37/40+, I can certainly say that while the 
new bigger boat can easily be single handed once  under way, and I would be 
comfortable taking her to a mooring alone, I'm not ready to go into a tight 
slip without another hand.  Does that keep me from getting out?  Not really, 
but there are times when I'd like to go out truly alone.  And yes,  there are 
many more systems on the bigger boat.  None of those concerns should apply to a 
30 vs a 27.  The 27 will definitely feel tight for 4, as it even was a bit 
cramped for 2. 
Just my $.02 worth,
Bruce 


Sent from my Verizon, Samsung Galaxy smartphone
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