In my opinion, $300-$500 is not going to be "entry level". You usually get the entry level packages for about $200-$250. Check Cabelas for those. I really think archery has one thing over buying firearms that is extremely useful, try before you buy. If you have $500 to spend, you are not very limited, you should get what feels right. Hoyt, Darton, PSE, Bear, the list goes one. There will be quite a few bows/bow packages in the $500 range, try as many as you can. Also, if it isn't for this year, wait until after the holidays. In the spring you might be able to get a last years model of something for a pretty nice discount from local places or from a Cabelas sale catalog. Try to get it early though, so you can have enough practice under your belt to be comfortable.

Good luck, it's an awesome sport
Brian