Cab...it does have a deep pan. I'll try removing some fluid and see if that helps. No trans temp gauge.

Jerico...I'm tearing up enough stuff as it is. No need to make it worse, lol.

Dusterkid...Lokar dipstick. I know it might not read perfect, but I tend to add fluid and then try the trans to see how it engages when I'm refilling it. Not relying only on the dipstick.
I wasn't on the brake long at all on any of my three passes so I don't think heat was a factor in the trans puking.