Chuck,
What do you think the ambient temperature would have to be that would keep our oil under 185 degrees? From what I'm thinking the oil cooler is going to be operating most of the time. 

Ride Safe,
Fired00d

That's really hard to say. I do know that riding in the rain helps tons because the spray on the oil tank really sucks the heat out of the oil.
The oil cooler gets the oil right after it leaves the oil tank and goes through the oil pump. the cooler cools down the oil and then it circulates in the motor, picking up heat and returning to the tank where it does most of its cooling. The oil enters the tank at the rear and makes it way up to the front of the tank, losing heat along the way. We measure the temp at the front of the tank, AFTER if has cooled down, and just before it is picked up and sent back to the motor.
There are several ways to drop the oil temp in the oil tank: Larger fins on the bottom of the tank, adding some fins on the sides of the tank, adding room for an extra quart. All of these would lower oil temps by either increasing the heat transfer from the tank or giving the oil more time to lose the heat it is carrying.
One note I'll add here, is that low oil temps are not good either. You want your oil temps to get up above 180 degres so the contaminants will be boiled off. If you never get the temps up high enough to boil off the contaminants, the oil will become corrosive and do more harm than good. Oil temps steady at 200 degrees in the tank would be nirvana. Then the temp could be dropped going through the cooler before being sent to the engine to lubricate and cool the internals.