I made a comment talking about why certain characters awakened on a post about Kaku. Someone said I should put my thoughts into its own post so here. (On my phone so formatting will be mid)

                    --How Awakening is achieved-- 

So, people seem to think that awakenings are just a show of skill but from what the series has portrayed this isn't the case. If it were simply skill, this would be implying that the Impel Dell jailers are some of the most skilled users, but we know this isn't the case.

Awakening depends not on your skill with a fruit, but rather how much you as a person synchronizes with the concept of your fruit. I believe it was vegapunk or kaido who said that awakening is when your mind and body are in sync

                                      --Examples--

●Simple perfect matches: There are some pretty simple ones, such as Luffy and Law. Law is a amazing doctor and his character focuses around that, so it makes sense he would awaken the operation fruit. Luffy is just like Nika, so of course at some point he would awaken that. These people just perfectly match the ideas their fruits express.

●More esoteric examples: Lucci was able to awaken his fruit because he truly lives the life of a solitary predator. He was raised to be a murderer without connections for all of his life, and often ignores the orders from his team and does his own thing. Lucci only cares about his hunt, regardless of how it affects others.

If you have questions about any other fruit users, feel free to ask