Personally I would keep the GMT-800. If you have a fairly clean example their values are starting appreciate. They have less electronics especially yours since it is a 99-04. Iirc 04.5 was the split when they added a BCM. 4L80’s aren’t the best but don’t seem to fail as often as the 6L80 or the 8speeds. We have 2500 express vans with the 6.0L at work. It seems every other week 1 of the 50 or so is down because of a transmission issue. Plus the 4L80 have been around long enough it can be rebuilt with better parts to live. The only somewhat major down side to keeping the older trucks are some of the OEM parts are starting to be discontinued. In my opinion the 06 and early 07 were some of last decent GM trucks built. 07.5-14 (recession era) trucks were garbage. Cheap and just shitty interiors in general coupled with whole LML CP4 fiasco. They are my least favorite modern era gm truck. 14+ got better with the LT and L5P engine families, a lot better interiors, up to date infotainment systems and ventilated seats. I’m fluffy and live in the south these make life better. Down side all the bells and whistles are tied to a module that’s expensive to replace and many require a relearn, pair, calibration, or ect. I got really close to buying a new 2500 in 2018 but decided to keep my 07. In 2020 I bought a 2013 that had a catastrophic fuel system failure. I fixed it and flipped it. A lot of people thought I was crazy for selling it and keeping my 07. To me there wasn’t enough of an improvement to justify keeping it. My 07 had about 15k less miles and you see way less clean GMT-800’s now.
My 07 now.
Dealer photo from 2013 when I bought it.