Let's face it, buying a big boat doesn't make any sense in the first place. It is much cheaper to get from point A to point B via car, train, bus, or airplane, and then at the other end, if we didn't waste all our money on boats, we could afford to stay in a comfortable hotel and eat gourmet meals in restaurants. Instead, many of us spend a lot of money so we get to scrape bottom paint off, repair engines while hanging upside down as the boat gets tossed about, and struggle to make five miles per hour in a zig-zag course toward a destination where the officials treat you like a piggy bank. Well, hopefully it isn't all that bad most of the time, but still, it really doesn't make any sense.
If you insist on banging your keel against the bottom like this, at least choose a boat that isn't ridiculous, which all too many people do. I would be rich if I had a nickel for all the times I've asked someone at a boat show what the draft and mast height is of a boat they are considering. It is incredible to me that people intending on keeping their boats on the East Coast don't make this a primary consideration. Basically, you really won't have much fun if you buy a boat that draws more than six feet and can't clear the many 65-foot fixed bridges over the ICW. Sure, I hear people say they never intend to do the ICW, but that means writing off more than 1000 miles of fascinating coastline, and one of the unique boating experiences in the world. And, even if you keep your boat in relatively deep New England, much more than six feet starts to really limit the number of small harbors you can get into. Move to the Chesapeake and it gets worse. Worse still in the Carolinas and Florida. In the Bahamas you cut your options in half if you need more than six feet. Five or four feet doubles the number of places you can go.
Then there are those who insist they want a bluewater capable boat, which most are with a modicum of care in choosing your weather. However, these bluewater wannabees think that if you don't have to crawl down a narrow companionway into the deep bowels of a full-keeled boat where you've got narrow sea berths you can wedge into, the boat is no good. This is despite the fact that for the next ten years they will be sailing it on the sheltered waters of the Chesapeake, sweltering through hot summers as the varnish peels off their eight-foot bowsprit. The qualities that might really make a boat great on the Chesapeake might include light air ability, shallow draft, great ventilation, good visibility from down below, low maintenance, etc.
When I go to buy a boat I write down a list of desirable characteristics and then I compare two or three or more different boats. When a boat wins a category it gets a check mark. I'll often have 20 or more characteristics. They include things like price, draft, height, layout, construction quality, condition, engine, tankage, sails, rigging, etc. etc. At the end of this culling process I am frequently quite surprised at the result. There before me is the winner of the factual comparison, and sometimes it is not the boat I have fallen in love with. It is a useful exercise.