JTT got trashed in the ToC. It wouldn't have had a prayer against The Second Tower, and if you swapped in Still in the Dark or Awe of She (which probably should be in the sixth spot for GG), they'd curbstomp it too, previous results indicate that. You picked a very weak example to make that argument.
And the problem is mostly that none of the OSTs that most people would argue as their favorite OSTs have strong 1-2-3 selections - that was the whole point of the way we did our setlists. We saved the best for last because not only would it have to face stronger competition, but because the songs that came into the final rounds were supposed to be the best the OST had to offer. That's how I went about it, at least. If you stick Umineko up against GGs lineup, it likely loses, too, because most of GGs songs are similarly well-received. It pretty much was just a terrible, terrible setup compared to a Magnificent Seven + Champion setup, or even the 1-3-5 | 2-4-6 style you mentioned. Hell, let me suggest something, Azuarc: run all seven nominations of AT2 and CC against each other while Umineko takes on GG, then pit the winner of those matches against each other. I'm willing to bet cash money that the results are wildly different, simply because the first three songs of Umineko and CC just aren't indicative of their strength, as they appealed more to the nominator than to universal tastes.
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Sburbopolis, Homestuck RPG: http://www.gamefaqs.com/boards/8-gamefaqs-contests/60981373