Sustaining your cruising lifestyle???
First I waned to thank everybody for all the great advice. I've been sailing for 10 years now but I am quite young (23). I don't have a lot of money, but I am preparing to buy a boat for long term cruising. Based on the advice from members of this community, I have set a goal for how much I need to spend on a boat and preparations, a realistic time frame to shoot for, and what to look for in a boat. That is not the problem.
I'm not worried about being able to travel long term as far as surviving on little money goes, what I'm worried about is when I want to buy a larger boat for more serious cruising. If I am sailing instead of working, how will I ever be able to upgrade?
I would like to ask how people here have made this possible? I don't really want to wait until retirement before I set out, but I would also like to be able to eventually buy a boat capable of major ocean passages.