Alrighty guys the problem has been solved!
Turns out the problem was within the smarty...
I was talking to a Cummins/Transmission expert and he told me to put the smarty back to stock and what'd ya know! The hang up was about 90% gone... So long story short it was all in the torque management. I turned the smarty back up and set the TQ M to 3 and it was back to normal... for the most part. It still hangs up VERY little up to around 16-1700 RPM, but it's because I now need to mod the TTVA motor to get it 100% back to normal.
Here's the technical explanation in case anyone is interested:
"Here is the problem, the 05+ trucks have the TTVA motor with a single non-adjustable program on them that ramp TV pressure based on a predertimed map of APPS readings. Whne oyu out a Smarty or other programmer on that changes the fueling curves you now have more fuel with less throttle position. All the preset shift points are now faulty because it takes less throttle to get to the same speed and under light\normal throttle gears seem to hang until you push it a little harder.
Under hard acceleration it is fine because hard throttle is past the presets and it just uses a default high value to determine shift and lockup.
What you need is as I suggested, a shift enhancer to ramp the TTVA program faster with less throttle to compensate. The other thing you can do is remove the TTVA motor, turn it upside down, remove the bottom cover, and advance the the gear thta drives the TV pressure 1 tooth. This gives you more initial advance TV pressure and a faster ramp to where the balance between TV and gov pressure is closer.
Works great on mine with the GM solenoid conversion. You will feel firmer and more frequent downshifts as you slow but its nice to know where the trans is actually at form my view.
BTW, the TTVA motor tweak is free where shift enhancers are $200-250. "