Thanks for the replies so far guys, keep them coming, I am writing down books to get from the Library!
I think (I hope) I have enough common sense to pull this off. I guess in the end there is only one TRUE way to find out
Being of my generation I realize I focus a lot on skills like how to use and fix a computer, and not much on more practical "hands on skills". I want to turn that around.
Would it be worthwhile to do something like trade in my spiffy Toyota for some beat up old car you can fix with a wrench, spare wires and chewing gum? Are there other such near-to-home projects I could take up that would be easily transferable to cruising life and forcing me to be more self sufficient? I guess the trailer sailor makes the most sense. I don't know why, for some reason, I feel hesitation about that... none of those boats really speak to me, and the ones that do would be too heavy for lake sailing.
(un)fortunately I am cutting cots by living with family. This is amazing for saving up my Sailing Kitty, but not so good for self sufficiency and scaling back on material things. Even if I don't buy stuff all the modern conveniences are right at hand.
I can't think of good ways that get me substantially out of my modern comfort zone without incurring a lot of extra monetary cost. But damn if I'm not gonna try.