Summary
The former undrafted point guard out of Wichita State has made quite a career for himself, and continues to improve each season. VanVleet made his first All-Star game in 2022, averaging career highs in points, assists, and rebounds in the '21-'22 season. VanVleet may not be a top 15-20 player in the league, but was comfortably in the top 25-35 range during that year. He struggled with his shooting early in the '22-'23 season, particularly his spot-up shooting, but was able to bounce back a bit as the season progressed. 
 
Offensively, VanVleet has become an effective scorer due to his ability to create separation and hit jumpers off the dribble. He's a 38% 3-point shooter for his career, and has hovered around that mark each of the last several seasons, although his 35% in '22-'23 was a career low. A lot of his shots are unassisted, off the dribble attempts too. He's not the same level of pull-up shooter as Steph Curry or Damian Lillard in pick-and-roll, but he's in the next tier and is a real threat in that regard. VanVeet is not someone that will carve defenses apart with his passing, but he can make the right reads once he creates an advantage.

VanVleet has become more reliant on his outside jumper in recent years. Only 17% of his field goal attempts have come at the rim over the last two season, according to Cleaning the Glass. Nearly 53% of his attempts have been 3-pointers over that time, which was a career high. Given VanVleet has always struggled to finish at the rim, and has consistently been a good outside shooter, that may be better for his efficiency. However, it could be slightly concerning if he becomes more one-dimensional as he ages into his post-prime.

On defense, VanVleet is strong enough and fights hard enough to guard bigger guards, giving his team flexibility to play him with another point guard, as he often did when Kyle Lowry was still on the Raptors. VanVleet was a big part of the 2019 championship Raptors, that essentially had no weak links defensively. He has good hands, and has consistently put up high steal rates for his career. 
 
VanVleet is 29 years old as a free agent in 2023, so it's possible that this could be his best chance at one more big contract before he exits his prime. However, as a borderline All-Star I would expect VanVleet to get a big contract, and could potentially even approach max level money. He didn't have the strongest contract year though, so he could end up having to settle for significantly less than that.
 
Cap Considerations
VanVleet has a $22.8 million player option for '23-'24, and if he declines that option he will be an unrestricted free agent with a $32.1 million cap hold and full Bird Rights, meaning the Raptors will have no restrictions on re-signing him. Since the Raptors will most likely be operating over the cap, his cap hold is not really relevant.

Depending on how close the Raptors are to the luxury tax after free agency, if VanVleet is brought back by the Raptors on a multi-year contract they could benefit from frontloading his contract, as it could give them additional flexibility in the future.

Since VanVleet's starting salary will be above the $12.4 million Nontaxpayer Mid-Level Exception, only teams with cap space will be able to sign him. If VanVleet and an above-the-cap team have mutual interest, a sign-and-trade could be worked out.