I have had an oil temp gauge on my last 3 touring bikes "08 "12 and now a 2015 RGSE. None of them ever ran hotter than 265*. That high temp was after sitting dead still for 45 min on a local toll road. My temps normally ran 235- 255* under normal operation. An oil cooler made about a 12* difference in temps on the road. In town an oil cooler made no difference at all. My new bike has the radiator and I seldom see oil temps above 248*. The 08 &12 were 103's with 255 and 254e cams. The 15 is 110 cu in and 255 cams. I tour on those bikes and spent many a long hot day with air temps between 95 and 103* F. Hope this helps. FWIW I use Amsoil exclusively in all three holes in all these bikes.

 

Mine normally stays below 230*,,, but has gone to 260-280* leaving out of Sturgis this year... Took this pic today when I hit 30k on the clock,,, you can see my oil temp gauge... it was 76* today and riding 2up for over an hour in & around town...
But 300* would've been my Pull Over temp.