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Ichigo's Getsuga Tensho didn't even scratch Grimmjow, so it obviously won't do shit to Nnoitra.
That leaves CQC, which Nnoitra will easily fodderize him in.
Ichigo got a huge ass powerup from Zangetsu and that wasn't enough because his hollow still had to save his life, that's the only reason he even tied with Kenpachi, because as we saw earlier, Kenpachi was able to fodderize a Shikai Ichigo.
Yeah but that doesn't matter. Nnoitra might have better defense than Ulquiorra but that's all he has. Ulquiorra is his superior in all other categories and his own style of fighting is more suited for battling Ichigo than Nnoitra's is.
The only chance for Ichigo is if he has resolve, which probably won't happen seeing the conditions. Grimmjow tanked a pointblank GT with no scratches whatsoever, so that attack obviously won't work against Nnoitra's Hierro. Ichigo could try to use his speed advantage similar to how Nelliel used hers, but that really won't work if Ichigo can't seriously injure Nnoitra. So I'd say Nnoitra takes this with mid difficulty due to his CQC skills.
I don't think that theory on how long hes been wearing it determining his power is valid. Too many unknown variables would need to be applied for it to be true, so as far as Im concerned patched Kenny is patched Kenny
What levels in strength do you speak of? Kennys striking power has always been high.
Its pretty clear looking at how Kenny could dice up the Espadas with the 1st and 2nd strongest hierros, being ranked 0 and 5th, while VB Ichigo could barely nick the 4th, and after a poweup, nick the same Espada Kenny amputated many times
FKT Ichigo, fully healed, is the strongest non-temp poweup Ichigo we've seen, not HM Ichigo...