Unless things have changed..
The MA excise tax on sailboats in very reasonable and the extra 3 feet will cost very little money extra. As for slip/mooring fees most marinas and clubs with moorings/slips offer either a 30 foot slip or smaller so many times even if you own a 25 footer you're paying for a 30 foot slip/mooring.
As for moving to Europe. If you are planing to move in a few years a 30 footer will have a better and easier re-sale. I've followed the used boat market for over 30 years and unless we can go back to the late 70's early 80's the "odd sizes" 25-28 are historically a much longer sale on the used market and many times they have to be almost given away at a yard sale price to move them. This is good only when you are a buyer but you CAN'T buy a boat only looking at the purchase price. To truly calculate COO or cost of ownership you need to factor in potential re-sale. Most people in the lower price point are looking for a 30+ foot boat. 25-28 is an odd size range because they are to big to trailer yet still have the expense of a 30+ footer as in to haul, launch and store them so most opt for a boat that will at least give them some living space and not be cramped when sailing with four of five people.
For example I purchased my Cape Dory 27 for 21k and then put tons of work and money into it. By the time I was done fixing this boat up it was, by a long shot, the cleanest 27 in the North East. Three years later, after being on the market for 14 months, I sold it for 16.5k. Everyone seemed to want the 30 not the 27 or 28 Cape Dory. In contrast my Catalina 30 was purchased for 22k and sold in two years later, in only two months for 28k. My Catalina 36 I paid 49k for and sold for 63.5k. Making money on boats is not the norm but if you are good with your hands, buy right (but not a basket case) and keep your boat spotless & in bristol condtion it will sell quickly unless it's a real odd ball. A clean well maintained boat is many times more important than the price to an experienced buyer! The inexperienced buyers are the ones buying the fixer uppers thinking they got a steal??
I'll say it again a 30 is NO more difficult to handle than a 27, 28 or 29 footer. They all have the same equipment but a larger boat will sail better and be far less tender. Contrary to popular wisdom boats between 30 and 36 feet are perhaps the easiest to sail of all boats and I say this with over 45k nm under my keel and 38+ years on the water.
I've owned over 20 sailboats in my life and by far my small sailboats like my Laser 2, Rhodes 19 & Cape Dory 27 were all more difficult to sail than my Catalina 30, 310 or 36..
I'm really trying to help you not make the mistake all to many people make and then later regret..
-Maine Sail / CS-36T
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Last edited by Maine Sail; 02-22-2007 at 10:00 PM.