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!