To add to A375's accounts of things that go wrong.
On one approach into a very short strip, as the F/O selected full flap it went asymmetric, with one side blowing full up as the other ran full down. The roll was interesting to say the least. Lucky I subscribe to the school of basic test flying that says when something goes wrong with an action, reverse the action if you have nothing to lose by doing so. In this case the F/O acted on my 'flaps up' call with alacrity and we got it level in time for a go-around to a flapless landing. The cause was a sheared actuater rod from the hydraulic cylinder to the flap linkage.
On another occasion the pipe that fed one of the hydraulic gauges on the F/O's sidewall burst and sprayed a fine mist of hot hydraulic fluid all over the cockpit. We got the gear down just as it ran out of fluid and landed in a very red, sticky mess. White uniform shirts were a total write-off.
As for the youngest DC3 pilot, I am sure that some military jocks would beat my record, but at the time I was an F/O at 21 and went left seat at 24. Flew it on and off with various companies over a 20 year period - interspersed with other types along the way. But everywhere I went, it seemed they had a couple of old WW 2 Daks that no one else in the company wanted to fly because of the whiz-bang turbo-props. Given the choice, I always opted for the Dak as I knew its time was running out. The turbo props would always be there for later.
Sad to see that some civil aviation authorities are legislating it out of existence. IMHO, even though it does not meet modern certification standards, it's nowhere near as unsafe as say, a Piper Chieftain or any similar light twin which is still legal to carry fare-paying passengers. At least it has firewall shutoffs and fire bottles etc and even a non-de-iced one will tolerate a light dusting of ice on the wings.