Welcome aboard Southpaw! Well, you have picked two good
boats to dream of! Here's what you do, look for a little, fun, fast
boat; I recommend a Laser. Take it out to the nearest body of
water that gets a breeze every chance you get. At first its a little wobbly, like riding a bike. But once you get the feel for how the
wind works on the sail, and how the
boat responds to it, you'll be scudding around in no time. And everything you learn on a
small boat will translate up to any size boat. But beware, you may get hooked and then make sure you have a good cash flow to handle it!

Good luck, keep us posted!