In Orlando, Oladipo played great as a point guard. His decision-making, aggressive play style, and passing were huge assets to the Orlando Magic. He fits the mold of a traditional point guard more than Westbrook.
In order to move Westbrook to shooting guard Billy Donovan must address a few concerns in training camp.
The most concerning issue is Westbrook’s ability to play off the ball. Since he’s not a great 3-point shooter, playing Westbrook off the ball has limitations.
The the solution to this would be one, or a combination of, two things; more ball movement and/or more weak side screening.