Let''s see if I can knock some sense into you.
First, $40k for a 27'' to 40'' boat seems fair, but may be a bit low for the upper range you''re considering. Even if you do find a 40'' boat for that price, it''ll probably need lots of TLC and major repairs, maybe needed sooner rather than later. :^(
Second, (IMO) a nest-egg of only $10k is woefully underfunded. One bad break (physical or mechanical) could cause you to go through that $10k in no time at all.
Third, I''m sorry to hear that your Dad and brother were not happy with the type of work they did. I''m sure that happens to many folks, but just in case you don''t know it "Life is Real". There are no guarantees that we''ll all have a pleasant one. The Preamble to the Constitution guarantees us "Life, Liberty, and the persuit of happiness..." That means you have the right to persue it, but it''s not gauranteed.
However, you are not your Dad or your brother. You may find work that is satisfying and rewarding. The chances of finding such a job increase geometrically as you increase your educational level. As you said, "there are lots of famous folks how have made it without a H.S. diploma." Well, I''ve got bad news for you - they are the exceptions to the rule. There are lots more (perhaps millions) who have made it big with a H.S. diploma.
Last, you totally ignor the fact that your health may not hold up over time. One bad fall or a bout with bad food and you could be layed-up for weeks - unable to work or worse, in a hospital with no way of paying for the care.
So let me ask you this - do you plan to be self sufficient, or do you plan to be a burden on society? BTW, if you don''t have a plan, then you''re likely going to be a burden on society. Since the rest of us think we will wind up supporting you, don''t be surprised that we think your ideas are poorly thought through.
Good luck (I think you''ll need plenty of it) and happy sails to you ~ _/) ~