08 Super Glide Custom V&H Slipon straight cut, Fuel Pak SE air kit. My average oil temp is around 265 on a 80 degree day. I have hit 300 on some super heated days in slow traffic, I run Harley synthetic and the Bike has always runs great. I change the oil every 2500 miles. I have added Xied but there is little temp change. (I have the digital dipstick not real sure how accurate they are) Considered an oil cooler but cant see the advantage if the coolers needs air to work, Other than adding a little more oil to the bike... So I was just wondering if anyone else is running this hot.

 

I don't run anywhere close to your temps, even here in Dallas where the summer temps frequently go over 100. And my bike is running 10.5 compression and additional fuel for extra cubes.....so it puts more heat energy out than a stock 96 inch motor. My cruising oil temps, enen when it is 100+ are about 245-255. Yes, at a light the oil gets hot quick.....but when I move away from the stop, the oil cooler allows the heat to dissapate quickly too.
Just last week I bought a cooling fan assembly and will mount it soon. Will find out if it can keep the oil cooled better at stop lights.

 

that seems a little high to me also..but I know about CT stop and go traffic..
from Meriden here.
dont have a oil temp gauge but the heat coming off the engine seems olny a little higher the my old water cooled goldwing..

 

If a HD shop put on the fuelpak the air/fuel mix is probably set to EPA requirements, maybe take it toan Indy to richen up the fuel mix and cool the cylinders alittle and in turn bring the oil temps down. A couple of things I do in traffic is don't crowd the car in front of me and watch where the exhaust is on the car in front in me (emits extra heat).

 

I also have the digital dipstick on my 06 and the highest temp I've noticed has been 264.