This is great information all. I am looking to get my first boat and I am reading and trying to absorb all the great information here.
The best advice I can give it to charter and/or crew on a wide variety of boats under a wide variety of conditions, this will give you a feel for different boats as well as give you the chance to sail boats you could otherwise not afford.
A boat is an extension of who you are, you don't need to impress anyone except yourself. While some people might prefer old style grace and simplicity others might get off on all the gadgets, gizmos and high tech cutting edge race based designs. So my advice is to decide what YOU like best, what makes YOU feel more comfortable, what fits YOUR uses best...then listen patiently to what everyone else says, nodding politely and gleaning any pertinent information to help you make your final decision. There is no BEST BOAT, there is a huge variety of boats out there, and for a "first boat" I would think you are not looking at a factory fresh 6figure or antique wood.
The economy as it stand will provide some good deals on used boats...one last thing remember, there is no such thing as a free boat.