I believe Madara takes this. Rinnegan would prove to be quite troublesome for Naruto to overcome as far his custom and perfunctory Rasangan attacks are concerned. Wood dragon can suppress Kurama's chakra in BM mode. Kakashi can mostly only stall the inevitable. Susano'o is far too large to be Kamuid by Kakashi. Can he do so with Kurama's Chakra? It seems a speculatory point to me.
Madara can even employ Katon attacks to counter Kakashi's Kamui. Also, the more chakra Naruto distributes, the more damage he receives, he would run out of the said time limit quickly. PS can be used in conjunction with wood dragon as well. This will triple Naruto's troubles, as not only will Madara sap his Biju chakra, but he will have to deal with the devastating slashes as well that will most definitely take out Kurama's tails. Any additional chakra supply to replenish the shroud's tails would result in further time reduction.
Another method to counter Kamui is through Mokuton clones as well. Honestly speaking, I believe even EMS Madara has a clear shot here. Rinnegan, Mokuton, and EMS would prove to be a colossal peak for these two to climb. As PS alone puts both of them at such a huge disadvantage. Madara can even put Kakashi under genjutsu and proceed to take him out. This method can be used for Naruto as well, who contrary to the popular belief, is not a perfect Jinchurki yet, according to his loyal bit ... I mean, buddy, Kurama.
The lag in recovery is easily exploited to use a few slashes to take out the shroud's tails. I dare say, low difference. At EMS level, I would still give it to Madara at mid difference, given his Susano'o feats and Katon attacks.