So, where to start, Ice? I will simply start refuting the parts of your post.
Why would I agree with you when this is a simple error in reasoning? You can't pigeonhole two different types of attack because of similar effects on a specific material. The ground is designed to be shattered with brute force, something Gaara's sand can't achieve. Depended by the target - in this case a human body - Gaara's sand proves similar way of damage Tsunade's brute force causes. I don't know where you get your comparison between Tsunade's punches and explosive forces from when in the end, both Gaara's sand and Tsunade's punch are designed to crush the respective target albeit being based on two different types of mechanisms. What makes Gaara's type of attack more effective in the end is the fashion of how it works. Unlike Tsunade's punch, which penetration power is depended by the opponent as well when the momentum of Tsunade's attack can be reduced by various conditions like the opponents agility, protection and the angle in which he is hit, Gaara's sand completely buries the opponent and thus taking all of his mobility and ways to protect himself while same time crushing the whole of his body with the high pressure of his sand. And if I compare what power Gaara's sand proved in comparison with Tsunade's punches against a human, it appears that former has the edge. Jiraiya once told that Tsunade, when being in rage, hit him up to a point he was left almost dead with plenty of broken bones (including ribs and his arm), demonstrating her brute strength while all under the premise of surprise effect and unawareness which didn't allow Jiraiya considering protection. As opposed to this, already Gaara'sYou must be registered for see linksproved more destructive capacity against a victim than Tsunade's punches all the time (when she had the opportunity of showing feats against Orochimaru and Kabuto) by squashing the target to a point he learned fast death and turned into a fountain of blood; a technique Kimimaro survived pretty much unharmed because of his properties [You must be registered for see links]. Sabaku Taiso is just a far stronger version that would turn a human to paste in a normal case with a pressure taken from sand masses which are covering a whole area. As for Kimimaro, in his second Juin form, he survived it again without the slightest harm.
You surely don't understand the mechanism of Kimimaro's body, as it differs from the mechanism of the body of a normal human. In order for Kimimaro to have access to his bones, latter have to find their way through his flesh and skin, tearing it up. Without a high level regeneration which allows him to render the wounds which have occurred when he takes or shoot out his bones out useless, this Kekkei Genkai would be useless. So this recovery is granted him automatically with his Kekkei Genkai [You must be registered for see links]. Seeing how he regenerates the wounds caused by himself as a side effect of taking out bones, there is no indication why it wouldn't work when the same damage is left to him by another person. Technically speaking, Kimimaro has a high level regeneration started from his skin up to his bones. Seeing how Kimimaro made use of his bones to survive Gaara's techniques unharmed by forming even bone armors to cover his whole body (note that his bones are harder than steel) a scenario in which Tsunade catches him off guard and hits him with a force that shatters his body and injures his vital organs (when Tsunade didn't even considered to use this level of her strength against foe's like Kabuto and Orochimaru) is rather not expected.
The extent of your imagination of Tsunade's capabilities are reaching a point where it is almost laughable to argue with you. You believe in scenarios of Tsunade being fast enough to rush Kimimaro up before he uses Sawarabi no Mai when it's enough to lay his hands on the ground for shooting them out immediately, even surprising the Uchiha brothers [You must be registered for see links] and Kimimaro being overtaken by Tsunade in the period of time he is busy taking out his spine or her blitzing an Uchiha over a distance of 50 meters (keep your response to this for the next clause). No offense, but you lose your reliability.
Once Kimimaro laid his hands on the ground, he will immediately start producing a high amount of bones, stretching over the whole battlefield. Here it doesn't matter if he was buried back then or not, because the fight against the Uchiha brothers and their insightful eyes shows that there is only a brief movement Kimimaro needs to create this technique. This technique will always surprise, as Kimimaro's attitude doesn't indicate what will happen until the bones start appearing all of a sudden from all directions. The time Kimimaro takes to grow this bones is so insignificant that both Gaara and Lee were overwhelmed by the fast broadening of the bone forest [You must be registered for see links] and saw the only possibility in flying out of the range, which crossed the whole area. As fast as the growth of the bone forest is, as incalculably it is. When you consider Tsunade to take out one of those huge, deep-seated bones (Kimimaro could grow them from a depth of 200 meters), you may don't consider that the forest keeps growing, impaling anything what is in its way and thus Tsunade, who stands right at their way, bothering to take out one of them and trying to play out such an irrational scenario you believe in. Trying to do this, she would do nothing but run right into the attack.
Destroying the ground is a scenario which also isn't happening. The depth the bones are coming from or reach in the ground can only be speculated at first view, but the fact, that Kimimaro used this technique from a depth of 200 meters and had a connection to his forest to escape this depth where he, according to Gaara shouldn't be able to move a single finger, is feat enough to guarantee the bones have a deep and firm anchorage, so the forest isn't stopped by Tsunade who will crush the upper level of the ground. While the ground beneath Tsunade's feet is going to be crushed, Kimimaro will just keep his forest growing to also shoot out bones at exactly this spot - considering the depth from which they can come, it won't be a hindrance for them to grow from a destroyed ground as well. Plus, Tsunade will may be limited to one move of such an extent as the speed of the forests growth won't allow her to act more extensive. Well, these are all assumption I backed up with Manga scans in the end, while it were mere claims from your side which are partially far from authenticity. Tsunade hasn't a real and logical counter for the Sawarabi no Mai, this technique is well suited for someone like her, who is limited to close combat with Taijutsu. She hasn't shown any significant Ninjutsu (apart from medical Jutsu) or other specific abilities which could support her against this bone forest. Mere Taijutsu and brute strength isn't useful against a technique of this form. Restricting this technique, I would doubt Kimimaro's win against Tsunade in the long run, but with this technique as his trump card, Kimimaro could take a safe win.
Tsunade won't give Kimimaro the time to pull his spine out? Really? Taking out his spine is a matter of little seconds. Considering Kimimaro possesses more speed and agility than Tsunade, he was doing good in dodging Gaara's sand and keeping up with Lee, who isn't only slightly faster than Tsunade in the databook (a canon source what you like to deny) but increased the speed and unpredictability of his attacks by a great amount when drinking his sake. Lee is also a CQC fighter and turns into a frenzy state when drinking sake according to Gai [You must be registered for see links]. Despite all this, Kimimaro was very well able to keep up with Lee and take time for creating weapons. Featwise, Tsunade has no evasion prowess at all, her fighting style is designed slow and linear bounded, which is based on dealing out and receiving a great amount of damage, which is outlasted by her regenerative abilities. It's enough to take a look on how much she received against Kabuto, Orochimaru and Madara, to say the evasion prowess of her is rather your hype than a feat.
Comparing Susanoo's sword with Kimimaro's Tassenka no Mai: Hana is like comparing apples with pears. You say the swords have more power when the power comes from Susanoo itself. It wasn't just one Susanoo that hit Gaara's defense but 5 at once, being able to overwhelm it. Plus, it was Gaara's strongest defense which thwarted Kimimaro's TnM: Hana which was explained by Gaara by collecting the strongest minerals from the underground to pressurize them into dense sand [You must be registered for see links] and nevertheless, Kimimaro's attack managed to penetrate this defense deep enough. [You must be registered for see links]. What you don't consider when comparing the form of damage left by Susanoo's sword and the spear is, that the amount of latter is indeed. Though having roughly the same diameter, Kimimaro's spear has all in all a considerably higher coverage. Susanoo's sword has a large but small plain, while Kimimaro's spear is thick enough to leave a hole that would cover one's whole chest, leaving a hole that is considerably larger than the one left when Kakashi uses Raikiri [You must be registered for see links], leading to unavoidable death. No regeneration can carry such an amount of damage, when your complete thorax is crushed along with your heart and other initial organs. That surely isn't comparable with a smaller Susanoo blade [You must be registered for see links] which pierced only her stomach.
And as for your scan with the hole in Obito's chest, I thought that the Manga already clarified it was just an illusion [You must be registered for see links] and when Kakashi really left a hole at Obito's upper body part, the story was that he was left at the blink of death. Surviving this even with regeneration would prove difficult as the amount and form of damage that is caused is too significant. How do you consider Tsunade to regenerate a hole of a footballs size? The amount of damage is just too great and there are too significant body parts which have to be restored. Mere logic let me consider that this is out of her regenerative capacities.
This is the most pathetic part of your post. By marking the exactly two panels of Tsunade jumping towards Madara and appearing before him, indicating she would have blitzed an Uchiha over a distance of 50 meters (when it aren't even 50 meters but less), you completely missed the chitchat Tsunade had with Madara within the time of running towards him and reaching him.
I marked for you the content in green which happened between the two panels you marked in red so that you can realize what actually happened.You must be registered for see images
During this period, they both managed to exchange 6 sentences. When Tsunade jumped towards Madara, she began to explain her technique in two sentences. After that, Madara totally calmed mentioned the part with the Jinton getting rid of the pollen and beyond that putting in straight that adding a medical Ninja won't change the outcome. At the end, Tsunade, who yet didn't reach Madara, had the time to point out two things. And then, she reached Madara, who decided to use Susanoo's ribcage to block Tsunade's punch, being aware this would be enough to stop her.
To you realize how absurd the idea was, that Tsunade would blitz a man who proved great Shunsin no Jutsu [You must be registered for see links] and is blessed with insightful ocular powers [You must be registered for see links] over a distance of 50 meters so latter could only insist on his Susanoo as a last resort, while not even having the time to use its full form when he already proved he can activate the perfect Susanoo instantly? It's hard to take you serious. These are the arguments you called flawless and impossible to counter in my presence? You should end the debate and leave as a fair loser.
Lee's speed has a slightly higher state in the databook (a canon source after all), he proved more agility than Tsunade and has drunk his Sake to purposely increase the unpredictability and speed of his attacks [You must be registered for see links]. Lee increased his speed up to the point he could even avoid Kimimaro's Dance of the Camellia [You must be registered for see links], where Tsunade's speed, agility and reaction clearly pales in comparison with and her fighting style is designed to receive the most hits used on her to outlast them with regeneration. Even then, in the end, Kimimaro got the upper hand against Lee because of his own unpredictability, where someone like Tsunade would easily fall to. In all appearances of Tsunade, she never showed speed feats in a battle that would be worthy more than a databook state of 3.5. I mean, If you think the databook stats have no weight and want to give Tsunade such great speed feats you wish, looking at Kimimaro's Dance of the Camellia, I could decide to give Kimimaro a 5 in speed, maybe a 5 in Chakra because he fought alternately against Naruto, Lee and Gaara.
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Anway, GG. Kimimaro wins with high difficult.
You are underestimating Tsunade + you know almost nothing about her abilities.
