Boat size is really a function of personal choice for the most part. Larger boats, while harder to manage in many cases, are also more expensive to own and maintain. A lot of the people who decide to go cruising are doing so to get away from the very materialistic/conspicuous consumer lifestyle that seems so prevalent today, especially in Western Europe, the Americas and the Far East. Some people don't need a LCD HDTV on their boat, others require a 42" plasma screen with surround sound. Some people will need more space than others, and others want to have a smaller, and easier to clean, maintain and handle boat. Some like multihulls, and don't want to live life at 20 degrees, others want the rail under and the spray in the cockpit.
Finding a boat that works for the type of sailing you do, in the waters you are sailing in is what is important. That said, some boats are better suited to certain purposes than others. If you like entertaining, and do mostly coastal cruising from marina to marina, a Hunter, Beneteau, or something similar might be the right choice for you. If you spend a lot of time anchored out, but like your space, and want to be "off the grid" then a big catamaran may be a better choice.
There is no right or wrong... Find a boat you love, and go sailing.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.