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Healthy is diffrent, so I won't really speak on that.
But if he's sick then he definately loses, even with Sasuke. Using Susano'O and Amaterasu at the same time is too much according to Obito, and using both made Sasuke drop Susano'O in cannon.
Amaterasu gets dodged and lower levels of Susano'O should be broken without difficulty between him and his clones. I doubt they can keep V4 up very long when Sasuke's limit with V3 is 10 minutes, and Itachi's would be even lower than that (if sick)
If they both have Susano'O then Sasuke at the very least gets blitzed by Shunshin given his reaction tike against Ay, and Itachi will have plenty of openings to be attack since using MS constantly has him coughing up up blood and seizing over.
The MS strain/chakra drain and them not being able to spam it is the big problem
If he's sick he loses, give him Sasuke and no he absolutely doesn't lose nor do they need to keep this up for 10 minutes because Naruto won't be alive for 10 minutes if he fights both of them.
-A blitz against Sasuke doesn't matter considering he has Susanoo, which Naruto can't get through.
-Itachi's illness gives him no room to blitz Itachi either unless you think Susanoo is going to drop when he coughs, which it didn't when he was on death's door let alone starting the battle off.
-Naruto isn't destroying or even doing anything meaningful to V4 (doesn't even scratch Itachi's) w/ anything short of COFRS, and if he stands still to make that Amaterasu lights both him and the FRS up. If Naruto tries to run around their attacks the entire match, then Sasuke just nukes him with Kirin and calls it a day. Itachi doesn't even need a full V4 Susanoo. V3 is enough to take all of FRS while keeping the user safe, add Yata and FRS doesn't even scratch Susanoo.
So Sasuke camps in Itachi's Susanoo and nulls all COFRS attempts with Amaterasu. Then he shoots Katon into the sky and obliterates Naruto with Kirin. Or Sasuke and Itachi both engage Naruto using their V3 and V4 Susanoo. Enton Kagutsuchi nulls any FRS Naruto throws at them, and anything that can't be nulled is blocked by Yata, then Kirin ends him like it would in any scenario he took both of them on.
But yeah. Sasuke can't solo because of speed. Itachi can't solo because of stamina. Put them both together and they don't need those things as Itachi can react to Naruto while Sasuke doesn't need to use Susanoo when Itachi's is there, thus he can focus on negating FRS.