The process to awaken a Devil Fruit is still unexplained but I believe it will be introduced to us in the Wano Arc.
Luffy definitely needs some sort of believable power boost in order to consider competing again with Kaido.
I think the process of Awakening has something to do with the interaction of seastone and/or ocean water. When a Devil Fruit user comes in contact with seastone, their ability essentially becomes dormant. To snap out or evolve out of that comatose state, the user “awakes” from the effect of seastone.
Coincidentally, the confirmed awakened ability users have direct and easy access to seastone. The jailers at Impel Down had contact with a ton of seastone, Doflamingo had seastone cuffs, and Katakuri may have had contact with seastone for a long period of time in his 48 years.
Luffy had basically overcome the weakening effects of seastone (although they are a weaker version).
If the jailers decide to swap his and Kid’s cuffs with regular seastone and they overcome the effects of it, do you think they’ll both be awakened in Wano?
*Theory by Threyethian