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Why do you worry so much about the details of your encode, if they are going to re-encode anyway and the "real" loss is going to happen on their side?
Alos I think using GradFun2db() or a similar dithering tool is pointless in this case - the dither probably isn't going to survive your 8-Bit encode. And, after that, there will be a second re-encode!
After all, I would simply go with "--tune film" plus a sufficiently low CRF value (or even "lossless" mode, if Youtube can process that) and then hope they won't screw it up too much...
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