I bought a little Canon Power Shot 10MP with 4X zoom for about $175. Takes nice pics, but it's not water proof. I keep it on a bino harness tucked into my shirt. It's out of the way, easy to access, and you can't drop it!
I have the Olympus Tom posted since Christmas. I think its great. The only drawback I've found is the buttons are kind of small when your hands are cold, but I don't think you will find small and light and waterproof and large control buttons. Its a good compromise.
I got a FujiFilm finepix z33wp for christmas and like it so far. My wife got it for about $140. Took a few pics out in the snow the other day and they turned out pretty well. It's a waterproof and on the lower end of your price range. Go buy some other gear with the leftover money.