I taught myself to fly, but then again I started with RC gliders. I built my first one (I think was called an Olympic 650?) and just started out by tossing it and landing it. A level hand-toss gave me 25 yards or so... Then I progressed to standing on picnic tables, stairs, etc, and finally to tossing it off the back-side of the high school football stadium bleachers.
Once I had that mastered I switched over to a high-start which gave me a 500ft launch or so. I think the worst that happened in that period was nipping a wing on a garbage can, and then later a flag pole. Nothing major to repair.
I then rebuilt the outer wing panels and added ailerons, and then added flaps to the inboard section. The tip re-build also added about two feet of span and decreased the polyhedral. Man that baby could soar! I eventually wrecked it by slamming it into the side of a mountain trying to land before an approaching t-storm. In all, that starter plane lasted almost 10 years.
Meanwhile, I was adding planes. I could seldom afford to by planes or kits, so drew up my own plans and scratch-built everything. I started with electric power, and hated it, so switched to glow. I just took any ol' 3-view I could find, and blew it up to fit the engines I wanted to use (.25, .40, .75). I went on to get a degree in art, so drawing was never that tough for me. Those included a sport-type plane that I built with 6 different wings (airfoil changes, span, flaps, ailerons, etc...), P51's and F4U's, an Ultimate Biplane, and others. I even had an RC redtail hawk that was going very well as a project, but then I quit working on it. It was giving me some issues because I didn't want a vertical stabilizer on it.
I've taught a lot of folks to fly over the years, and I've got to say that the buddy-box cord idea rocks. It's saved many a plane... I didn't use it of course, and didn't destroy any planes learning, but I took a gradual approach. I knew how to land first, fly second, and take off last. It's tough to do that with a powered plane, unless you have help.