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First of all, you did not mention what knowledge is involved here and whether or not Kakashi is aware of Tsunades techniques that give her super-regeneration?
That being said, ill try to give my view.
I think Tsunade has a far better chance than others have suggested. Tsunade would presumably activate her regeneration ability from the start given how strong Kakashi is, and even if Kakashi knows about the regeneration, it would be far harder for him to bypass it than others have suggested.
Kakashi may be faster than Tsunade, but the idea that Kakashi could just stroll in and decapitate/slice her in two feels silly(for one, Raikiri does not have enough power to slice off an entire torso without repreated hits). Not once have we seen Kakashi do that to anyone, and Tsunade would be ready for that regardless. And if Kakashi does not know about the regeneration or if Tsunade say jumps or something causing Kakashi to miss, then Kakashi likely loses. Tsunade could basically grab the hand that had pierced straight through her, and then either touch Kakashi and screw his nervous system or just use her superstrength to get an instant kill with a fatal blow that Kakashi could not survive from. The Raikiri wound would then heal, giving Tsunade a victory.
Even if Kakashi used a feint such as a clone to check things out, this would not necessarily help. Kakashi has always had chakra problems (though admittedly he has improved recently), while Tsunade has lots of chakra. If it comes to a longer battle, his only hope would indeed be an instant kill through Raikiri to the brain or somesuch, but that would not be easy, given that he would have to avoid Tsunades attacks or even her touch, while driving a raikiri through her brain while avoiding Tsunades attacks. And don't forget that Tsunade would know about this, and would do all she could to avoid such an attack, even if she had to sacrifice other bodyparts to do it. Super-regeneration is actually a very good advantage, IMHO.
Just for reference, Kakashi has speed stat only 1 higher than Tsunade, so a total blitz where he drives a raikiri through Tsunade in a way where she cannot do anything to avoid it seems unlikely.
Whats the difference other than the location? Regardless, prettymuch the same as scenario 1.
Kamui is incredibly hax technique, and Kakashi has improved with it recently. He would use Kamui to teleport Tsunades head to some other dimension, killing her despite her regeneration.
EDIT: I thought I would say this. While I do agree that Kakashi is the better shinobi than Tsunade, the idea that he could basically stomp her like a bug is exaggeration.
Kakashi takes first two scenarios with little difficulty and he takes the third scenario with moderate difficulty. I doubt Tsunade will summon Katsuyu but if she does, Kakashi can counter with bunshins + undergournd raikiri...GG.
That automatically invalidates the regeneration arguments for Tsunade,as she couldn't think of keeping up for an extended period of time,with a spontaneous thinker like Kakashi who on the other hand isn't one dimensional like the kage but can opt for round about tactics like bunshin feints,underground diversions,genjutsu andmore importantly has shown the proclivity to aim for the vitals,in 2 of his showcasings(to the heart and to the brains);but I'm not in any way suggesting an attrition war
And needless to say if she his hit with such techniques she's going to inevitably die as she's just a regular human being;a regenerating shinobi but ultimately still limited by the binaries of human anatomy itself(as per her showcasings),unlike shinobi like Kakuzu and Oorochimaru who have transcended to said limitations
Of course I'm not saying she's not going to counter Kakashi,but given her shallow arsenal and predictability,her deficits would eventually lead her to her downfall,considering the opponent she's facing
for the several time an old post of mine addressing the regeneration:
Originally Posted by Myself
Tsunade's Regenerative properties
Databook entry for the Sozou Saisei:
Created by the greatest of medical ninja, Tsunade, this is the ultimate regeneration technique!! By releasing a large amount of chakra at once, the body's cell division is forcibly stimulated, reconstruction all organs and all tissues making up the human body!
If this technique is used, a body whose vital organs are so gravely injuried that it cannot bear it any longer will be instantly restored to its uninjured state...
The bold,is the key to understanding the limits of the regeneration
Now we've seen that she can recover from fatal wounds such has the stab from Madara,and all of that fits perfectly with the jutsu's descritpion,but we also need to consider that she can't grow an organ if it isn't there anymore,she can surely regrow it it's partially wounded
To put it in Layman terms,she isn't Piccolo from the DBZ,she can recover,but not recreate an organ from nothing,because her regeneration is limited by the human anatomy in itself
Byakugo;it basically operates on the same principle of the Sozou Saisei,but automatically.But in battle that matters little,because it doesn't give any noteworthy benefit as far as regeneration goes.Maybe the lack of constant hand seals leaves Tsunade's chakra pool more room to operate
"Hey but Iceman,it's said that she can heal instantly,why can't a new heart be regenerated?"
If he heart is ripped out,there's nothing to regenerate to,and without a heart there's no blood,thus no oxygen pumped to the brain and soon after the brain also dies permanently.With the brain dead there's no organ instructing the heart what to do,and thus end all the regeneration shenanigans
"But Iceman,a human body actually lives some instants after the heart stops beating"
Yeah that's true.But what is required for the brain to operate properly is fresh blood,and with the lack of a heart pumping it,it's activity shuts down and so the rest of the body,because they also happen to require fresh blood and oxygen and not the recycled one that would be present by the time her heart is no more part of her body
Conclusions and implications
The conclusion we can draw from the showcasing of her regeneration are that it operates on the binaries of the human body,meaning it can accelerate the healing to the instantaneous level,but it can't create a limb or organ from nothingness