" Ok, so tomorrow morning I intend to sign up for the 8-day Maryland School class in the Caribbean in March."
DO NOT SIGN UP FOR THAT MARYLAND SCHOOL of Sailing & Seamanship coruse at this point in your sailing career. That would be a total waste of your time and money.
We all come to sailing with different goals and differing amounts of understanding about what sailing about and about what it takes to own a sail boat. As I read your posts it comes through loud and clear that you are brand new to the sport and have no clue as of yet. That part is perfectly okay, we all had to learn somewhere, and to a great extent you have come to the right place for help.
But here's my point on the Maryland School of Sailing and Seamanship. I am the first to admit that there is no one right way to learn to sail. Everyone who comes to this sport decides just how good a sailor they want to be. They may not make that goal but they get to set their target.
For some, the goal is simply to get safely in and out their slip. For those folks almost any school will do, But for the rest of us, to one degree or another, we all ascribe to be more than that. If you had some basic sailing skills under your belt and you aspired to learn how to push big clunky boats around, then perhaps a sailing course like Maryland School might prove helpful.
But having taught at least 100 people to sail in my life, I can tell you that the learning curve on a boat like an Island Packet is so steep that it would be an exercise in frustration if not futility to try to learn from scratch how to sail on a boat like that.
My advise is to slow down. Take the power squardron or Coast Guard school to learn the basics; rules of the road, navigation and weather. Wait til spring and take a real sailing course that will not only get you a certificate, but also teach you boat handling skills.
If you must learn to sail over the winter try a course Colgate Offshore Sailing School's learning to sail course which is taught in Florida in Colgate 26's, boats designed for the purpose of teaching sailing, and its a sailing real course where you might actually learn to sail. Sailing Lessons, Sailing Courses & Sailing Classes from Offshore Sailing School
As they say on the site: "This course is also a great refresher if you’re just getting back into sailing and is the most comprehensive learn to sail sailing course there is. Three to five day schedules available at all Offshore Sailing School locations."