Thanks for all the input...Except for Scott!

The larger oil pan is out. I will wait for higher temperature days, ride it and watch it. If it does not exceed 300 I will leave it alone and ride. IF it does get over 300 on regular basis, I will then look at a "hot day, high elevation map with a little less aggressive timing.
Last resort will be oil bud or whatever cooler the aftermarket or Mother HD come up with. You know they will, eventually.
Did not mention my tuner, because I get tired of "eating s%^t over using Thundermax on all my bikes for the last 11 years.

I have four units currently in operation. They really do self tune and I have never had a problem with one. I cannot say the same for PC tuned motors.
I have even had a couple on Dynos over the years and they checked the tune and AFR, all was good. Yes they can do a SLIGHT bit better with a full dyno tune, but it WORKS great for me. I quit chasing the dyno sheets a while back. I look for good torque on baggers and cool running builds. All my other builds have no wet heads but oil coolers, except the Vrod with a Trask turbo and intercooler but no oil cooler, Just a BIG RADIATOR! I do not recall ever seeing oil over 290 on the worst days.