I can't remember how many times.
EDIT:
Okay, that was 2 hours ago, I am finally all the way awake now. Now let me see if I can remember now. There was my first file, who was good. Then my second file, evil. Then the third good skill person. Then evil skill person, then good will person, then evil will person, then I did that again so twelve, then I tried neutral will users so 13, same thing my first and second time on the lost chapters so 19, and then there were those three files I was working on before the Xbox crashed, so I think it is around 22 files total, and 19 finished. I almost never finished a file, I just kept getting stuff and getting stuff, then got bored and finished, then kept getting stuff.