bluesmoke328:
Coding Badly, I saw your comment about the Adafruit library component having "holes that are way too big". Were these even bigger than the package outlines used by the Arduino boards?
Yes. Significantly larger. The Adafruit Library footprint looks like it was made for a 220 volt connector (i.e. "huge").
The footprint is supposed to be for this part...
I believe it is similar (identical?) to the jack used on the Uno. The footprint in the Adafruit Library is more than twice the size of the actual part. It is still possible to solder the jack to a board but certainly not easy.
This is my attempt to correct the footprint...
http://forum.arduino.cc/index.php?topic=135596.msg1268085#msg1268085
Looking closely, there's a lot of solder filling those holes!
That probably indicates the footprint is wrong. The holes in the board should be slightly larger than the pins on the connecter. Obviously, more solder is required than, say, LED leads but it should not be necessary to "fill those holes".