The fact that the submissions have to be mailed in will cull out a lot. The fact that the deadline is in 2 weeks will cull a lot. The fact that what you think is cool and what 100,000 other people think is cool is very different will cull a lot. The fact that the OGL has proven that 9 out of 10 of the people that have the gumption to get somthing out can't spell will cull a lot. The fact that being a writer is a lot harder than wanting to be a writer will cull a lot. The fact that many gamers can't separate story from mechanics will cull a lot.
I feel that the chances of an entrenched freelancer taking the cake are slim. The reasons they are entrenched are 1) they can write, 2) they take the time to write, 3) they are creative. That is pretty much the only reason. If you have that then you can do freelance work.
Aaron Webb