I aM RETIRING SHORTLY AND WANT TO BUY MY FIRST BOAT. I will probably move to the Hilton Head area but am open to going farther south if the boating advantages are decidedly better. I hope to cruise perodically up to two weeks at a crack. My questions: What are the parameters I should use in selecting a boat? 1. What is a good size to learn on and make my rookie mistakes? 38-42' has been suggested. 2. Age? I want to buy used. I would like to stay below $300K but don't know what that gets me. I can go higher 3, Quality or Quantity? Quality or size? 3.5 Aft cabin or express, etc? I like going fast on toys but my wife is more subdued 4. Resale: if I wake up in 2-3 years and discover a new hobby, what original purchase limits my downside and lets me sell my boat in a reasonable amount of time? I would expect to take a hit but a wise original choice might limit the damage. 5. How much boat would I need to cruise to the Bahamas? I want to give myself a good initial experience so as to maximize the chance of making this a lifetime hobby. I am sure these newbie questions have been asked many times. Any help or direction to other posts/sites would be appreciated.