I am one of the "buy a boat" group.
Grab a trailerable dinghy/laser for home up north and sail the crap out of it on a local lake or puddle. Small boats are great teachers because you get wet if you make a real mistake.
If your dream is to have one to stay on down south than find a friend with some knowledge and get one, hang around and make friends at the marina down there and you are sure to find someone experienced to go out with until you are comfortable.
Life is short