@Redux91
Sorry, I'm late to the party and am reading through this thread right now. You made lots of great points, but I just wanted to clarify on the financials.
Kawhi can sign for 5 years worth a total of 190M if he stays with Toronto. Since he didn't play for the Raptors on his rookie contract he doesn't qualify for the "time of service" bump on top of the 190M. Only the Spurs could've offered him that deal.
With any other team the most he's eligible for is 4 years and 141M.
Here's a pretty good breakdown of how it all works (way too complicated):
NBA Free Agency 2019: What Are Max & Supermax Contracts? | Heavy.com
EDIT: Actually, I'm not sure if he'd jump to 35% of the cap after his first two years on a potential 5 year contract with TOR. If he did, that would yield him another 10 or so M extra. One needs a damn accounting degree to calculate NBA contracts' breakdown.