I'm looking through SitePoint now and I'm actually rather impressed by the functionality and surprised at how well the contests seem to work, even for much lower dollar amounts. I have no doubt that you'll get some good entries and I imagine watching the logos come in is a lot of fun too.
Agreed. I had been there in the past, and it seemed pretty slapped together...but they've used their success wisely by investing in better technology. The contests system is, so far, top-notch.