I admire your spirit and setting of goals. I''ve always been goal oriented,and have found that it keeps me focused. You do have your work cut out for you to achieve the items you''ve mentioned. I think you have a good plan, but if I may, I''d like to offer one suggestion.Once you learn the basics of sailing, you might want to consider purchasing a small day sailer if you live close to the water. You can usually pick one up used for around $1K. If you decide to go this route, get one that has both a jib and mainsail.The experience of working and trimming two sails will be very valuable to you later when you upgrade to your 28''-30 footer. As you''ve already realized, you need to spend as much time on the water as you can. Good luck!