About existing games, yeah modern sims like Session and Skater XL actually use the physics-based methods you're describing rather than the trigger zones you'd see in older Tony Hawk games. They rely on spline-based detection to find edges in real-time.
The problem with screwing an engine like that onto GTA V is the geometry. GTA's collision meshes are optimized for cars and pedestrians, not the precision a skateboard needs. You'd constantly run into invisible gaps. To make it work, you’d essentially need a script constantly raycasting from the board to detect edge-angles and apply a sticky force once a threshold is met. And that's just to handle basic movement; it doesn't even touch the nightmare of implementing a trick system or custom animations.
Honestly, it would be much easier to rip a section of the Los Santos map and remodel it for a dedicated skateboarding game than to try and force GTA’s engine to behave that way.