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I'm pretty sure as long as he has cells and vampiric essence left he can regenerate, and Okuyasu's swipe won't be encompassing enough to delete all of Dio at once.
If Okuyasu swipes his brain he's gone but that's an specific situation
In-character means that DIO would probably see him as a normal human and since he wouldn't be able to see The Hand he'd probably get close, making it easy for Okuyasu to swipe him.
Diavolo would have to constantly time skip to keep himself safe so any hit he lands on Wammu would just regen. But Wammu wouldn't be able to damage Diavolo either. Inconclusive.