What Type of Jira Workflow Transition is Best?

Well, it's Jira so of course, the answer is, It Depends!

And to be honest, some of the explanation has to do with personality as much as functionality. Some people like definitive paths, others are more free form and like the flexibility. 

So, what are we really talking about here? We are talking about the movement of issues or work items in Jira through the workflow or across the board, if you like. These steps in the workflows and columns on a Jira board relate to Statuses in the workflow. And Statuses are mapped to columns on a board.