I'v been meaning to suggest something for this script for a few weeks now. As I have yet to try it (never seen to have the time lately

) I dont know if my suggestion is usable or not, but it may be something you could use.
I'v mentioned the FOW (Fond of Writing) tool here a few times, and even tried once or twice to incorporate it into a script but the programs just wont interact in the way necessary. I think it would make a great addition to this script as another type of task/punishment, as the FOW program is designed to create reports to be sent/given to the dom by the sub (if the sub has one of course)proving it had been done.
If Liz want to look it up and give it a 2 minute once over (it is a really simple but effective program), I think it could really add something to what you are building here.
I'v been playing with the program on and off for years and I keep going back to it as my favourite sub training device. There is nothing better for getting into the correct mindset than typing lines (especially if you dont know how much longer or how many lines you have to go). It also has pretty much doubled my typing speed and quality over the last few years, so happy side effect.