I'm not going to be discussing the ENnies much with this post, except to remark that they are the industry standard when it comes to awards. Origins awards don't have the same kind of bling in the eyes of the gaming public. The fact that the ENnies are backed by the largest gaming con - Gen Con - and one of the most trafficked RPG fan sites - EN World - certainly doesn't hurt. They also cover (in theory) every corner of the RPG gaming universe.
For the OSR we have the Three Castles Award. Most don't realize this, but the Three Castles Award (which is judged by panel of judges that are from the gaming industry) is judged primarily based on design merits (I'm sure other biases also come into play, as such is human nature) . Also, the publisher or a third party has to submit copies to the NTRPG Con for the entry to be considered.
Pretty much all of the yearly winners and finalists from past few years of the Three Castles Award have been the cream of the crop but there are many titles that don't get recognized that most certainly deserve recognition.
Some folks in the previous ENnies post joked that the OSR should have "Tenkies" or some such. Besides the fact that the jokingly proposed name is horrid, any such move to a recognized OSR Award for Best of "X" needs to include the whole OSR Community (beyond just blogs and G+.) Preferably, it would include forums and publishers big and small. I'd rather see the community decide on the top 10 in each category (assuming there are 10 in a category, we are a niche within a niche) and an esteemed panel of judges picking the top three. It keeps it from becoming a popularity contest and lessens the effect of stuffing the ballot boxes.
Oh course, this is just stuff being thrown out there for critique and suggestions. There is no real game plan except for realizing there is no game plan.
And no, I'm not volunteering. This is all firmly in the category of "what if?" at the moment ;)