Re: need advice on boats to purchase
Boats at the smaller end of your spectrum would be better for your wallet, easier to maintain, teach you more about sail trim, and cause less damage if you screw up.
For what you describe, an autopilot, a wind generator, and a water maker would probably not be helpful, so don't get all excited about these spendy add-ons.
I agree with others in that your first boat, should not necessarily be your last boat.
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USCG Licensed OUPV Captain, ASA 101/103/104/105 Certified Instructor - Also certified in Recreational Marine Electrical Systems