All great points above. What I find fascinating are all the various configurations of the H27. My 27 has wheel steering and an installed head. The wheel and head probably make it feel more substantial than it is. Many people who sail her comment that they're surprised to find a wheel and head on "just a 27 foot'er."
I agree that it is a brick, but a very safe, stable brick...especially when the wind pipes-up. Christmas Eve 2003 on San Diego Bay with 35kt+ winds by the evening. A few friends and myself had it heeled over 30* or so but were never concerned (until we had to put it in the slip...). The 27 is a great, seaworthy boat. I do feel that it sails slower than its rating, although I think this has a lot to do with a deck stepped mast, mid-boom sheeting, lack of jib tracks, tracks to far outboard (toerail), thick lead keel, and so on. But for the family, cruiser, single-hander I can't think of a more solid 27 foot boat.
I agree that for the time, money, and hassle involved that the 33' seems like a better option...but that's all things being equal.
-The 30 will cost more for slip (although my marina charges me the 25'-30' price), haul out, transportation, etc... As far as maintenance is concerned, I think that if you do most things yourself then costs should be comparable to a 27. I mean, sure, lines are longer, sails are bigger and there are a few more systems...but your everyday repairs like sealants, epoxy, hoses, varnish and such should really be about the same.
-More systems can add cost and complexity, but one could always go the other direction and simplify: I do fine with my solar shower and hand-pumped water system.
-Three extra feet really DOES make a difference. I upgraded from a 23 to my 27 and it felt like a hotel by comparison. However, now a 30 or 33 looks so nice......and my friend with an O'Day 18 thinks my boat is the Taj Mahal... -
-Remember the most important thing with a boat, the next boat you buy is totally dependant on your ability to get rid of the boat you own. Owning TWO boats at the same time is a curse from the Devil himself.