I don't even know what awakening truly is, so it's hard for me to tell whether awakening happens at once or step by step. But here's my logic: pre-timskip Luffy mastered gear 2 and 3 after learning haki, and I think that similar stuff will happen with gear 4 and 5. I think Luffy will reavil gear 5 against Kaido which will have drawbacks as well, but then he will awaken his DF in the fight against Blackbeard where all the gear drawbacks will dessapier.