Personally, all my life i have chosen to live on hills. Just on last Friday, we had a very heavy 24-hour rainfall that was as heavy as I can remember, anywhere. The streams and road gutters (typically 3 feet deep here) were like a flash flood.
Farther down bore the brunt of it. We were fine. The only scary part is that there had been no other rain in August, so there was a concern about landslides. Fortunately we are on the side of a little extinct volcano, so it is rocky.
Planning is good.