I think Luffy should get awakening in order to beat Kaido. If we assume Kaido also has awakening, then I don't see Luffy beating Kaido without himself having awakening.
What would also be cool is if Luffy starts using conquerors attacks with his awakening. I think that Luffy should come about, especially after the all crazy shit Zoro does, especially if he's going to beat Kaido. Luffy fans got that to put him at that "yonko" lvl. Luffy is getting that great pirate status after this war and some of his worst generation peers like Law and Kid possibly will get that title (maybe). Also after this fight with Kaido, I feel like if Shanks, Rayleigh, and Oden saw that fight they would get Roger vibes from Luffy, they'd realize they were witnessing the same greatness they saw before in Roger back at God's Valley. This will be Luffy's God's Valley, winning the war against a yonkou alliance of Big Mom and Kaido.