I'm chuckling a bit because I get this feeling of consternation every time I run into something that doesn't go very smoothly. For instance, learning I was using the wrong kind of hammer for roofing saved my wrist from breaking. I've been collecting woodworking and carpentry tools and teaching myself as I go. If you really want to develop some intuition for what to use and when then learn about the basics of carpentry and wood working: routing, planing, joining/jointing, sawing, drilling, gluing, sanding, and finishing. The difference between machine and hand tools often comes down to surface area and/or density (that may not be holistically correct, but it satisfies my bar for a rule of thumb).