John in NM
"2. I've found that I'm reading and re-reading the books that were recommended to me as I started. Things that I missed or didn't understand open up more and more as I go back after having tried (and often failed). Many times I will have missed something or disregarded something as unimportant that really helped when I went back and read."

That is precisely the point I was making with an earlier analogy to mathematics. Problems I couldn't solve in HS seemed trivial to me towards the end of college. Much of the problem comes down to context - you don't always realize that a technique is a vastly easier method until you've struggled the hard way a few times. I too have noticed the same thing in WW'ing.

"3. I feel very ill-prepared for the wily ways of wood. I'm not sure if I could get much from books but even then there isn't much in the ones I've read that start me down that road. "

Here again is the importance of gaining experience. Mistakes are not some tragic waste to be avoided at all costs - they are how you learn most effectively, a crucial part of that "ah-ha!" moment when you figure out the way to avoid the mistake next time around. Even after more than 20 years of this hobby and a rational understanding that there will always be things I wish I'd done better, I too often feel ill-prepared. The trick is to not let that stop you