No. 2: Wing defense
The 2019 Toronto Raptors could absolutely shut down any opponent defensively. Kawhi Leonard was the greatest perimeter defender of his generation, Danny Green was a lockdown guy with plenty of championship experience, and Kyle Lowry and Fred VanVleet were strong options in the backcourt. That doesn't even count OG Anunoby who missed that playoff run due to injury.
This year's roster does not have the same defensive bona fides, nor even much of any. Jakob Poeltl is a solid rim protector and Scottie Barnes is a defensive playmaker with excellent instincts, but they are the team's power forward and center. Who is going to defend All-Star guards and wings on the other team?
Gary Trent Jr. and Ochai Agbaji are receiving the task, but neither is a lockdown option nor defensive playmakers generating steals and rotating well in team defense. Gradey Dick is both a rookie and tall enough that he is best deployed on larger players. RJ Barrett and Immanuel Quickley have defensive chops but the reality is much more disappointing. Bruce Brown has been bizarrely awful on both ends of the court for the Raptors since coming over in the Pascal Siakam trade and is unlikely to be on the roster next season.
Of all the players likely to fit into the rotation beyond this season, there is not a true difference-making defender on the perimeter other than Barnes. That's a problem that will need to be solved, whether through drafting someone, signing a 3-and-D wing in free agency or buying low on a player with potential.
Winning a title means going through multiple teams with powerhouse scoring threats on the perimeter, and that means Toronto has to acquire the means to slow them down.