Jed I tend break my fifth string quite often. I am not sure why. I just assumed it was from the constant retuning of my 5th string. I use my railroad spike so that I do not have to tune up or down more than a couple of notes, but it still seems to break often.
But I am now starting to wonder why. Maybe I have a sharp or rough bearing point that the string is resting on. I'll have to see at what point this string is breaking. Maybe I am doing something wrong like how I wind the string. I could be creating a kink in it or something.
Or maybe there is a sharp edge at the tail piece? Not too sure. But if I don't find it soon, I am going to invest in a 5th string manufacturing company.

Mark those guys on stage, they are just trying to look cool.

Bonnie Bonnie