I think the radiatior mounted trans cooler would be the most help. Keep in mind that deep pan doesn't really do much but hold more fluid. Sure, it takes longer to heat up, but it doesn't really SHED heat much better than a standard pan. Will it hurt? Certainly not, but for the money I think you'll get better cooling function from a cooler.
I intend to live forever. So far, so good.
'99 Wrangler Sport: 2.5" Old Man Emo lift and shocks, adjustable trackbars, Quick-Disko sway links, rollin on 31" BFG A/Ts