I was roughly 5 when I saw this movie, so it had to be from 1994 or earlier I’d say. I remember a grumpy old lady and her family. I believe some teens went to visit or live with her. She was mean to the boy and didn’t want him skateboarding inside. At one point she turns evil like a demon and rides his skateboard I believe. Down some stairs I think. There’s some kissing cousins, and the guy peeks at the main actress changing. I think the main actress is playing the older sister of the two teens. At one point they’re all in an office listening to someone’s will and what all they inherit.