The problem with rely on the knock sensors to allow running on lower octane fuel (than what the engine was designed for) is that the ECU will keep trying to run at its normal timing (and boost for a super/turbo charged engine) and will detune itself as a RESPONSE to knocking - it doesn't just stay detuned as it will keep testing to see if it can run as it is supposed to. This means that the engine will knock at a reduced rate just as you have surmised and damage will only be slowed, not prevented.
What your friend needs is a remap that runs with retarded ignition and lowered boost.
Resident grumpy old fart
VW - Metallic Paint, Radial Tyres, Laminated Windscreen, Electric Windows, VW Alloy Wheels, Variable Geometry Exhaust Driven Supercharger, Direct Unit Fuel Injection, Adiabatic Ignition, MacPherson Struts front, Torsion Beam rear, Coil Springs, Hydraulic Dampers, Front Anti-Roll Bar, Disc Brakes, Bosch ECU, ABS
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