I briefly tried to play that game a couple times, and you're right. It doesn't work well. I just upvote stuff I like. If it happens to be trending already, then I upvote it. If I like it and it's undiscovered, then I also upvote it. I'd love it if that's how everyone upvoted, and then if a lot of curators made a point to look for undiscovered material. I don't see it changing too much from the way it works now, though.
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That's the best way to do it, though I'd recommend thinking twice about upvoting a Trending post. The voting power saved could be more effective voting on undiscovered material.