Summary
Trent really broke out in his second season during '19-'20, establishing himself as a legitimate NBA wing. Trent's eFG% was a great 58.5% that season, led mostly by his 43% shooting from 3, but he was also above average from every other part of the court as well, according to Cleaning the Glass.

Trent's outside shooting has dipped a bit since joining Toronto, as he has hit just under 38% of his threes. Some of that is due to Trent taking more difficult, unassisted shots after being traded to the Raptors, and them not having the same level of spacing, but it's also likely that he was unusually hot in his early seasons, and it's unlikely for anyone to continue that level of shooting as their usage increases. After generally continuing to increase his scoring each season, Trent is averaged under 14 points per game in '23-'24 after topping out at over 18 in '21-'22.

Trent is a little more than just a "3-and-D" wing, as he has some off-the-dribble ability, and he has fared decently as a pick-and-roll ball-handler at times. He has the ability to hit shots off-the-dribble, but his 46% 2-point percentage is below average. Trent takes some difficult shots, and while some of that is bad shot selection, some of it is just due to his role and the lack of off-the-dribble creation for the Raptors. He probably plays more of an on-ball role with the Raptors than he should.

Trent isn't really a creator for others, as he has never averaged more than two assists per game, and has consistently put up extremely low assist to usage ratios, which shows how often a player got an assist given how much he had the ball. He at least doesn't turn the ball over. 

If Trent were a little bit bigger you'd feel better about him defensively, but he still has the size and quickness to defend multiple positions. He's a little small to defend the bigger, stronger, elite NBA wings, but the Raptors have generally had plenty of better options to do that and even in another situation I would not expect Trent to be tasked with that role. He gets a good amount of steals, and his 2.2% steal rate in '21-'22 was in the 91st percentile for his position, according to Cleaning the Glass. That rate continued in '22-'23 but dipped a little bit to only slightly above average in '23-'24.

As a starting level wing or high-level bench player, Trent should get sizeable offers in free agency in 2024. However, the fact that he exercised his $18.6 million player option for '23-'24 may mean that he wasn't looking at any big offers in 2023 and he did not have a great '23-'24 season.
 
Cap Considerations
Trent will be an unrestricted free agent with a $28 million cap hold and full Bird Rights, meaning the Raptors will have no restrictions on re-signing him. As Trent's cap hold exceeds the salary he will get in free agency, his cap hold is not really relevant.

Depending on how close the Raptors are to the luxury tax after free agency (or on how much cap space they need if they operate under the cap), if Trent 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. However, doing so could cost them cap space if they operate under the cap.

For other teams, if Trent demands a starting salary of more than the full $12.9 million Non-Taxpayer Mid-Level Exception, only teams with cap space will be able to sign him, unless a sign-and-trade is worked out. However, it's possible that Trent could be had for the full MLE or slightly less.