It's fun to branch out a bit. I feel like I've held a lot of tricks up my sleeve for a lot of years, and 'Ex-Girlfriends' is a good way to show another side of me.
If you don't give your kid freedom to make choices with money, including stupid choices, he'll make plenty when he gets to college.
In choosing any role, I ask the same questions: what kind of part is it? is the role challenging? does the director have a vision? is the story moving? etc.