I think another difficulty is that a substantial portion of the "good" content out there is probably created by monks. So we have kind of a conflict of interest if we start handing out awards.
If merlyn writes a good article about Perl, as he has been known to do, and we all vote to give it an award, that's fine. But like I said, monks create a lot of good Perl-related material on the web. Over time, as every Perl article that a monk writes gets the PM Seal Of Approval, it starts to look like we created an award to give to ourselves.