Anyway, script content aside, I can confirm a similar scripting problem as the OP here. I was scripting for EX at the time, so I'm not sure if this persists in Aika's patch, but I'll dig up my old trigger/script files and try it later.
I was attempting to write a script that triggered if a girl's PCLove stat hit 100, where the girl would approach the player in his office (lair?) and confess their love. I had planned to have it give an obedience, spirit, and confidence boost. Similarly, if the player got a girl's PCHate to its furthest extreme, I'd intended to do one where the girl attacked the player (though the worst case scenario would either have her running away with some gold).
Using a trigger xml in the individual girl folder, I was never able to get this script to fire. And doing it globally, I wasn't 100% sure how to get it to a) trigger on a specific girl and b) to make sure that it could happen with more than one girl, but not have it happen every turn for a girl once she hits 100 PCLove.
I know you have your own plans for scripting in your patch, Aika, but if you build on the existing trigger system, it might be something worth checking out.