All good advice. You could also consider a plan where you sail - race with a crew and get lots of experience. You will learn a lot about different boats, people and conditions. (Note; on the people thing, don't waste time on a boat with screamers, shouters or captain Bligh). With increased experience, you could learn to care for and deliver or skipper boats for others. Costs are low, exposure and fun is high, total commitment is low. With enough on-water time, you can also get your USCG captain's license. Good hunting. Here is how we did it.
I sailed small boats from the time I was ten. (505; 470; Prindle Cat; Bucineer; Super Porpoise; Sun fish; Hobie; Laser; MC Scow; Cape Dory 10) Later, after college and just married, I joined a race crew and raced my buns off on big boats all around the Great Lakes until my job took us away after about 25 years. I kept the Dory and Sunfish as my knock-about boats and then added a 20 ft Tornado Cat. At this point, I feel like I could walk onto just about any boat. We are now close to retirement. We rented in the Abacos a few times and love the tropics & Caribbean. We searched for Florida (Naples or so) for a retirement venue but found real estate, taxes, insurance totally impossible. On a whim, I suggested we follow my cousin's lead and live aboard & circumnavigate. She said "find a boat". Six months later we were having a hurricane damaged 58 ft Camper & Nicholson ketch delivered to Grand Rapids, Michigan. The restoration is well under way & after three years, we plan to launch this spring. We will exit the Great Lakes by the St Lawrence. (photos in my gallery http://www.sailnet.com/photogallery/.../ppuser/159746