I think you need to do a complete "cost of sailing" analysis. I suspect you are grossly under-estimating the costs associated with sailing. The cost of the boat is only a small part of what it''ll cost to go sailing. Even a well maintained boat will require major repairs at some point (hopefully, later rather than sooner).
Good food (meaning good nutrition) is not easy to accomplish for extended cruises, and is usually not cheap either. Health will play a big factor as you age. Even routine hygene can become costly if you don''t take good care of your teeth, skin, feet, etc.
Finding work may at first seem easy, so long as you don''t expect much. However, there may come a time when you won''t be able to find work, or your body won''t allow you to do work you were once able to do (e.g. - arthritis, weaker muscles, etc.)
You sound a bit selfish and naive. You come accross as someone who wants it now, but you don''t want to put in the effort to get it the way it normally done, meaning studying, graduating, working hard, meeting your responsibilities to society, then saving, then enjoying the fruits of your labor.
BTW, about 35 years ago, I was in your situation. I chose to graduate from H.S., join the Navy, get some training, take advantage of the GI Bill and go to college to get a B.S. and then a M.S. Then I gott a good paying job, save up for the things we needed and wanted.
As of now, we owe about $30k on the house, we''ve put two kids through college, own our boat and all our cars and furniture, and still have plenty of time to enjoy the fruits of our labor. If I had to do it again, I wouldn''t change a thing.
The choice is yours. You can do what you''ve said so far, or you can try to do it my way.
Good luck and happy sails to you ~ _/) ~