I generally jump at the chance to play simulation games like this, but the first time I heard of PM2 was at Something Awful...hardly a glowing recommendation and it made me avoid the game.
I came across it again while browsing here, decided to give it a chance, and wow, I'm glad I did! VERY addictive game.

(In fact I have to wonder if the Something Awful guy was even playing the same one, or if he was just on mind-altering chemicals of some sort...)
The first time I just messed around seeing what the different choices did and wound up with a dance instructor with too low of a constitution to ever be very successful, though the second time I started to get the hang of things and tried to make her bratty and evil. She got arrested, stole from me to buy dresses, lazed off at work, and eventually became a prostitute.

(I don't know what it says about me that I have so much fun trying to ruin the girl's life...)
Next time around I used the Mad Eddy cheat to get money to keep her at school and on vacations without having to work. She eventually won the dance, cooking, and painting competition, occasionally worked at the caberet but still had extremely high refinement, charisma, and sensitivity, chatted with all the people at the palace...and still became a prostitute.

I admit I was hoping for a more manipulative or powerful evil sort, but from the tips I've read on this board maybe I should get the next one into adventuring?