You can spend less than that $300 until you get going if you use GoogleAppEngine, where you'd only end up paying if you get higher levels of usage.

Rackspace cloud will cost $10 a month for the basic server if you need to not use java/python, as it sounds like you might need to. You theoretically can do Ruby on GAE via a java implementation, and php I think...

If you need web design, you're going to be a little short there likely to get it done, but you may be able to learn enough to get going there.