Just another update. After adding ducting to the parallel cooler, in 90 degree heat, I was seeing a max of 280 degrees (down ~15 degrees from only the factory cooler). When it was in the low 80s, I was seeing a max of just about 270 degrees.
I was measuring oil pressure and during one turn it consistently dropped to ~20psi. I'm assuming because of oil moving away from the pickup. Hard to see from the video - 3 clips of the same corner back to back, but you can see the gauge drop when I turn left.