As for the DATA... Here's were the results from a ~20 min round trip with the cooler completely BLOCKED off:
Highway pull IATs down to within 12F or so of ambient
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Highway steady cruising (A/C off to clarify) - IATs stable between 15-20F above ambient
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Another highway pull: IATs down to within 10F of ambient
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So obviously something we did helped. Now was time to pull the CAD designed block-off plates (Cardboard Aided Design) and re-test again.
With the oil cooler UNBLOCKED:
35 to almost 40F over ambient IATs steady state highway cruising. Again this is A/C OFF.
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Highway pull - a bit over 25F over ambient
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Another highway pull - IATs were just shy of 30F over ambient.
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So we've finally figured out that the oil cooler is the problem (placement, size, etc). Obviously a bunch of people run them, and many people run them in this very same location (including Area Motorsports). I do think that being located on the passenger side is less than ideal because that is the cold side of the intercooler - if that side gets heated by hot air from the oil cooler, it's got no chance of ever coming back down.
Mounting on the driver side would still allow a better delta-T if the pass side stays cooler, but realistically the correct option is to duct the existing cooler down and under the car or relocate the oil cooler somewhere else which is very tough on a DSG R. Venting downwards isn't great for aerodynamics, but it is probably the lesser of two evils when there are coolers occupying both fenders already.
Also it is worth noting that oil temps indicated on dash with the cooler UNblocked, were stable 185-190F the entire time. When the oil is closer to 250-270F entering the cooler on track at VIR... it is throwing a LOT more heat into the intercooler. I can see why people might not see any "problems" on the street and then without running data think everything is fine on track.