Somewhat related, I actually would prefer two plain text files with instructions about where to put them rather than a smart package that knows what directories they belong in. I have no idea why I feel that way. Must be the Luddite coming out.
I see that you have some ideas so I won't try and elaborate on my report, but I will add that there are no SKILL entries in the relavent planner_user.txt files.
Tangentially, mafia seems to have an implicit naming convention along the lines of user_tag.txt as in the prefs, mood and session files. Any particular reason why you chose to reverse it? Since I am running three characters out of the same directory I am pretty used to sorting by filename if I want to clean things up.