You can see a very good offering of scopes at Orion Telescope and Binocular http://www.telescope.com/
Long focal ratio refractors are the best for planetary viewing, shorter focal ratio reflectors and refractors for deep sky. Whatever you pick out, get a really solid mount. The stuff at Walmart, etc. is junk. A bad mount will spoil any desire to pursue star gazing further. I’d go for a manual mount rather than an automated one. You will learn to locate stuff (not that hard) and it takes time to set up the auto mounts. Also, get a mount with slow motion controls. Not sure if you can squeeze this into $500 but you might come close. Feel free to Freepmail me with any questions. I have about 8 small scopes - all refractors.
I had the Edmund Astroscan for a number of years, and this can't be beat for ease of use, with almost zero setup time. It is limited in power, though, and I wanted to step up.
I would be wary of the computerized setups. I think you have to go top end to get the real advantage of these. I think it's ironic that so many "beginner scopes" actually require a deft touch to make them work because of the low cost and skimpy construction. I say wary, as I have been wary, and never owned one! So that's just my opinion. To me, part of the fun is learning to spot, and this involves basic knowledge of the sky, so what are you out there for?
That's another caveat. Observing the sky is actually a rather refined enjoyment, and many people are spoiled by the dazzling depeictions they see on TV. This started with Sagan's COSMOS series, but it's just gotten worse since then.
Good luck!