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U_U
Minato
Minato already beat Obito and if it weren't for Kurama, he would've kilt him. You say if Obito plays it smart, Minato is a genius everything he does in battle is strategic. If Anything Obito would need and not Minato.
Madara
His chakra reserves alone would qualify him as the clear winner between these two. His jutsu are arguably the most powerful jutsu we've seen thus far. His speed easily rivals that of killer bee and itachi if not surpasses. removing all other Uchiha powers that com with MS, Madara's perfect Susano'o would demolish the enviroment they were battling in, it is unstoppable so and thing Obito throws at him wouldn't work.
Hashirama
Basically the same as Madara but without the Sharingan. And if nobody Hashirama could pass Madara's Perfect Susano'o then obviously Kamui is a walk in the park.
Kakashi
He is also genius and he has Kamui as well. If his chakra reserves were higher he could beat Obito with minimal chance of being killed.
Nagato/ Paths of Pein
Nagato has all the Powers of the Paths but in one body. All Mighty push would keep Obito from hitting him with anything. The summons would keep Obito at a distance increasing the effectiveness of Almighty Push. His ability to absorb chakra would make it pointless to attack with jutsu leaving him moreless vulnerable to genjutsu.
The Separated Paths however would prove more difficult because they're multiple bodies with linked eyesight making a surprise ineffective. And genjutsu would ultimately work on some of them but not all of them. Trying transport them to the other dimension wouldn't, because they'd just do what Kakashi did, and attack what part of him was in the other dimension with thus making even more dangerous for him to fight and use Kamui.
Obito already beat Kakashi senseless, Kakashi gets stomped.
Nagato loses, Minato loses, EMS Madara loses.