A lot of people who are associated with him, like Pompeo, Noem, and Pence are clearly preparing candidacies of their own.
I wouldn't be surprised if Trump leaves his possible candidacy hanging over their heads until shortly before Iowa, just so he can enjoy watching them tear each other apart.
Then after he jumps in he'll skip the debates, because why bother, they're going to be too terrified to go after him anyway, plus being on a stage with them is just a reminder that he actually lost and is technically their equal as non-president, and we can't have that.
At that point they'll just be angling for VP / heir apparent. After he runs the table in the early states, they'll all drop out and endorse him.
I actually think he wants to debate other candidates, its one thing he clearly enjoys, ripping people to shreds. He'll do anything to go face-to-face with a RINO and call them names.