My lay understanding is that S&S isn't worried about the high oil temperatures reached through normal operation. The engine can handle it. The issue is the oil. Each time it reaches a certain temperature, its lifespan is reduced necessitating shorter interval changes. An oil cooler would therefore extend that interval.
My understanding too is that once oil heats, say above 225F, the engine loses 20% hp, but no damage. So keeping the temps in the 170F range would preserves consistent power delivery...or so say the Porsche air-cooled guys.
IF both statements are true, is the greater risk in oil not achieving, say 170F quickly or in exceeding 170F on longer distance rides? I guess I'm having trouble understanding how a cooler which is thermostatically controlled and keeps temps at a consistent 170F or so operating temp can be anything but helpful??