Here's my question. If the oil in the tank is 275 degrees, then how friggin hot is it right when it is exiting the motor? That moment it leaves the motor would be the maximum temperature, and the most important temperature to monitor. The oil gauge is in the front of the oil tank. The oil enters the tank in the rear and then moves to the front, all the while cooling down. The temp you are measuring is the temp just before it goes back into the cam chest then filter and cooler.
In short, the oil dip stick, and oil gauge in the front of the pan, is not reading the maximum temperature the oil achieved. It's a number, but what it is actually telling us is rather vague.
Absolutely correct, the dipstick or the dash gauge both measure the oil temp in the pan after it has had an opportunity to mix and cool somewhat. Rest assured, if you could measure the oil temp at the piston rings, you would really be worried.
I haven't seen anything from H-D on what they consider to be the normal operating temp for the 110" engines, but they did indicate normal operating temp is 230°F for the 103" engine on the '05's. That is with the bike running down the road, not sitting or barely moving in traffic. As soon as you reduce/eliminate the air flow across the engine and oil cooler, the temp is going to climb fairly rapidly and there is nothing short of a big fan or shutting the engine down that is going to change that. You can't run the mixture rich enough to offset the lack of airflow on an air cooled V-twin. When I previously commented in this thread that 275°F was too high, it was with the caveat that I wasn't talking about sitting in traffic.
Fortunately, top quality synthetic oils like Amsoil and Mobil 1 can handle bulk temps in the 300°F range without suffering thermal breakdown. I would never consider running anything but a top quality synthetic in one of these engines.
Jerry