I want no script asking me questions.  Post-facto errors for omissions are fine (and if I have to positively say no in the input file, that's fine).  tkinter is right out.
 
If you *also* want to make a script that asks questions (or even a tkinter ap), that's fine, but it should not be the main interface, it should be a wrapper.

One thing I really don't like about the separate file approach is that you lose the obvious chronology.  It's probably not a blocker, but it is definitely a disadvantage.