Compared to building an OS and support libraies, building your own plane is trivial. Flying it may take balls, though. For the best example I know of: short video at http://www.joostconijn.org/film/vliegtuig/index.php.
The guy built three planes. One didn't take of, one crashed, one brought him across Africa in short hops with landings at rebel-occupied airports where he didn't always manage to announce his arrival.