I found that other then the expense of everything being larger the bigger boats are actually easier!
I think your on to something Free.. In this economy I can't see how it would hurt you to take some time off (other then the resume gap) and its not as hard to move to a more restricted life style now as it may be after you start getting serious extra cash in you pockets. Do what you want while you can as once folks get married and kids start coming many folks trade their desire for adventure for the idea of stability & their lives are easily lost to their kids. We are trying to balance that as I figure the kids are going to enjoy what ever they grow up around so we each have some activity that's important to us, while doing kid activities, and trying to spend time as an overall family. Its hard..
Personally I would suggest working for a few years, keep your expenses minimal and then go out on your adventure, it will give you some time to see what a grown up life may turn into and while your gone you can reflect on what may really make you happy?
Currently Sailing a Allmand 31