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That's a great question!

While I would love to track the actual results in terms of traffic etc, it's impossible due to the time it takes for search engines to rank content. So, I can't pick winners based on traffic (as that requires ranking).

I also know that most people are strangers to SEO and that the majority of the people never have optimized content previously, so it would be unfair to just look at the actual optimization of the posts.

With those things in mind, I am more likely to look at the structure of the posts, the information within, internal linking (how the links to my post (and other posts?) are done) and after that, I will pretty much just have to make a rough guesstimation for what the potential results might be and pick winners based on those things.

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Maybe you can add that to your post so people who are interested to join this contest have a clear image of how the winners will be chosen.