I have thought about cooling the oil on this beast but after long consultations with a local S&S mechanic we determined that it would be overkill. Mind now, I live in southern Vermont with no large cities and miles of roads devoid of traffic lights as well as having very temperate weather during driving season.
The other issue is that you are carrying 6 quarts of oil versus the standard 4 quarts on any bike. That helps in a large part. It also gives you more latitude between oil changes.
I have changed out the oil since the very beginning and it still looks and feels great after 3,000, 4,000 and 5,000 miles. It does get pricey as the oil universally recommended is the Mobil Synthetic for V-Twins. Good stuff.
If you are due for a service then please ask your dealer to see the engine diagnostic. It will show you temps, rpm's used as well as many other things of interest. What I learned from mine was that there were occasional spikes of heat as well as revving the motor hard but, for the most part, in actual use this car is loafing along.
