Ahoy Joe 206, Big Red 56 here, I reccomend you buy anything you can get your hands on including a project boat that required you to work on it before you sail. Nothing is going to prepare you except experience. I suggest you start small and trailer what ever you buy. Centerboard is just fine however considering your age and marital status I suggest something two people can enjoy. Any sailing dinghy 16'' and up ought to do. Highlanders are nice, many small boats that are poor sailers by other people standards are just fine to start out with. The point is buy anything now and get started. I do not reccomend any thing as big as 25 + feet or any fixed keel boat because the problems and limitations in your travel restrictions will make the whole pross to cumbersome and less enjoyable.( Time and prep and expense) I have never spent more than One thousand dollars for any of the boats I own and there are plenty more where they come from. If you see something sitting in a yard covered with leaves stop and ask.You''d be suprised what great deals are just sitting there for the asking. To place anyone in your position in a "J" or similar racing class boat is ludicrous and expensive. You will be a poor sailor for the simple fact is you don''t know the difference and you''ll never learn starting off at the top. What you will become is another elitist arrogant and shallow sailor. If your plans for the future are sailing take my advise , otherwise you''d better have plenty of money to buy ,maintain and sail your dream. Big Red the Pirate of Pine Island.