Just an update on my issues, after a couple other failed attempts I had them to remotely take over my computer, took them several tries and about 45 minutes but was finally able to get it to load in my laptop. I was then able to get the data logged and sent off the file right before full blown winter hit here, which is about 6 months long.
I dreaded putting the new tune in because of all the issues associated with downloading the program previously but the first warm day I gave it a shot. I had to download the EFI Live once again since it seems to get updated weekly and the previous download is not compatible again, but once that was done the files downloaded into the handheld and then uploaded into the Tahoe.
I've only driven it 3-4 times since because winter hasn't fully left us yet but there's a noticable difference in the shifting patterns, holds in gear longer and shifts firmer, which takes care of the lackluster mushy to quick factory upshift points. Definitely has a different exhaust note when warming up the car and feels peppier, I live in the city so no wide open throttle checks as of yet but feels good in the seat of the pants regular driving so far.
Hopefully we can get a few more rainy days to wash the salt off the roads followed up by some sunny days to warm things up as well to get some total driving experience with it.