Sit down and make a list of things you want to do with your new boat, where you want to go, who will be there, your time frames, and even little stories about a perfect day on the water, money
involved, and everything that you want to do, that has to do with your boat. Revise the list several times.
That list will tell you what to buy. Spend your time finding a good deal on the right boat, not fixing up a junker,
Masts get unwieldy at about a 24' boat.
Take the advice of people who do what you want to do. You will get a lot of negativity from people who use boats for other purposes, and even more from armchair sailors. Racers are good people, but if you want to cruise
, listen to the cruisers, and vice versa.
Match the boat and trailer to your vehicle. A mismatch can be deadly.
Do it! put a limit on your pondering, and get what seems best. $2,000 is not a lifetime commitment. A year from now, you can always sell the first boat, and buy something that will fit your now experienced opinion of your needs. Do it now, and a year from now you will be the experienced sailor that "Joe Shopper" is still asking about the perfect boat.
Get your wife's input. If it suits both of you, she will be more likely to sail. If it is "your thing", you will be soloing a lot.
There are times when a 120' crew boat of a big shrimp slab trawler
cannot "handle the coastal Gulf" Any 25' sailor has to pick his times.
Some of the twin keel sailboats are big and stable, and can be anchored in the shallows, but you will pay with speed and pointing ability. The sleek narrow boats sail best, and the spacious, easy riding ones are a bit slower. Your choice.
Deep keels are great for racing
, but for trailering, gunk holing, and Florida bay cruising shallow boats are best. My centerboard Morgan
28 draws 36 inches, and less would be nice. Here, you lose about 10% of the bay for each foot of draft
, starting with the nicest part. Swing keels and centerboards will be shallower, and a very shallow boat has less need of a dinghy
, a big advantage.
Decide what you want and find it rather than just pick from todays "good deals".