OK... final update. I spoke with the folks at Techlusion (TFi) about my settings. They agreed that I was most likely at the best settings. All of my settings were slightly on the rich side, so no heat issues coming from that angle. Any increase in the green pot would result in a great decrease in my gas mileage (currently 38-40 mpg solo).
I went ahead and added the H-D oil cooler, and I noticed a huge improvement. While riding today in 95+ degree temps, I never saw the temperature rise above 242 degrees, and it often remained between 210 and 230 while cruising.
I feel a lot better now (keeping in mind that my machine only has 4,200 miles on it). My only real complaint: H-D should have made the oil cooler standard equipment.
Thanks to all on the board for your help and ideas!