Overheating -- Corrective measure questions.

A lot of good suggestions here..

One thing I noticed. You have a 10 x 12 inch aftermarket trans cooler mounted in front of the radiator? That's 120 square inches of air flow being partially blocked. If its a 26 " rad then almost half of it has an obstruction to airflow in front of it.

The factory did not do it this way, even for Hemi Cars! The rad had internal provisions for trans fluid cooling.

I'll be the first to say I'm speculating here but this stood out to me as a possible problem.
I have an electric fan (from a Chevy HHR) cooling my radiator. The radiator does not have a transmission cooler in it so I have combo trans/oil cooler sitting flat(no blocking the rad) with its own electric fan. I run about 190 degrees on my 418 stroker.

Edited: Should have been 190° not 290°