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.