[NoahsCaya]

I don''t have any experience "living on the hook" but when faced with the same dilemma my friend and I (me 31, he is 32) decided to just do it! We bought a 35'' sailboat (found a deal too good to pass up) and are in the process of selling everything we own to move aboard and learn how to sail as we head south from Newport, RI (where the boat is now) and venture off towards South America via the Bahamas and others (we start in June).
I must add though that we are both very skilled in land survival and have even been guides and instructors on land so the idea of living VERY simply is not new to us. We also have done some considerable travel in North and South America. We actually prefer the simple life over the rat-race of society where it seems all we ever do is "live to work" instead of "work to live". Our hope is to take things much more slowly and focus on conserving our money and enjoying our surroundings rather than looking for the latest and greatest electronics that will fail at the most inopportune time anyway.
One last thing to consider is your girlfriend. My girlfriend doesn''t get along with my long time adventure buddy and unfortunately he has more pull (I have known him for about 10 years and her only 1.5) so he is my sailing partner instead of her. It is a tough choice you may be faced with if her desires aren''t the same as yours. Other than that, we might be making a big mistake but I would rather regret something I have done than something I haven''t done, I ain''t skeerd! (dang I wish I had that pirate lingo)