head to head
Pilotwings 64 asks more than Grand Theft Auto: San Andreas, and the gap is execution.

Optimization · Practiced Mastery
A sprawling open-world crime epic with RPG-style character stats across a whole state.

Execution · Practiced Mastery
Flight school score-attack where smooth control of quirky aircraft earns medals.
Grand Theft Auto: San Andreas leans Optimization (Practiced Mastery); Pilotwings 64 leans Execution (Practiced Mastery).
Pilotwings 64 leans clearly harder on execution.
Grand Theft Auto: San Andreas
Flying school and drive-bys need decent hands
Pilotwings 64
Precise stick control of gyrocopter and jetpack
Same score on reads - which means the number cannot separate them. The difference is in what each one asks of you.
Grand Theft Auto: San Andreas
Gang AI is scripted, never adaptive
Pilotwings 64
No opposition, only score targets
Grand Theft Auto: San Andreas leans a little harder on variance, though the gap is small.
Grand Theft Auto: San Andreas
Territory wars and traffic add light randomness
Pilotwings 64
Courses fully fixed
Grand Theft Auto: San Andreas leans a little harder on optimization, though the gap is small.
Grand Theft Auto: San Andreas
Stats, gym, weapon skill, and routes reward systematic play
Pilotwings 64
Optimal lines and landings reward study
A matching score does not mean a matching test. Two games can both sit at 10 on execution and demand completely different things of you - which is why the reasoning above matters more than the number beside it.