Plan on two boats...
one for now and one in five years. I suspect you will be ready for a different boat when you move to the Gulf.A lightweight trailerable has many advantages/disadvantages compared to a heavyier boat. Our 1988 MacGregor 26D only weighs 2200 lbs, including trailer. (Not including motor, anchor, stuff, etc.) It carries 1200 lbs of water ballast, which we leave behind and don't have to burn gas to haul down the road. We launch and recover in a couple feet of water and a six cylinder 2 wheel drive will pull her without problem. Several will disagree, but, our M26D will not survive a storm on open water. To stay light it gives up strength and I would expect a hull separation in a storm or a prolonged heavy gale. A hurricane would be suicide, as it just wasn't designed for 30 foot seas. I'd do the day-run to the Bahamas, but nothing overnight on open ocean. After 31 years at sea and dozens of ocean crossings I know how fast weather and luck can change.Enjoy the ability to learn the sport and easily tow a light trailer boat. You've got an excellent highway system that'll expose you to many sailing venues. In five years, sell her for at least break-even and move up to a boat that'll handle the seas and weather on the Gulf Coast. There's one heck of a difference between a lightweight 26' trailerable and a 26' bluewater boat.Besides, once you get hooked on sailing you may end up buying a big boat and taking a 10 year weekend. Speaking of which, has anyone read about the Ottawa family's 1999-2003 circumnavigation? After only six afternoons on a 22' boat they sold it and bought an old 42' cruiser and took off the next spring. They wrote a book called, "The Voyage of the Northern Magic", which is a great read for any sailboater. Check the link for a quick look at their story.