My 2006 Denali XL has a trans temp gauge to the left of my rpms. I keep a constant eye on my trans temp pretty much whenever im driving. Even on flat roads and just normal driving. But that's because I just had to have my trans rebuilt @ just over 83,000 miles. Not happy with that fact. But oh well. The trans temp,is a nice feature to have. I'm planning on adding a second trans cooler soon. So hopefully that will help keep the new trans cooler and more well maintained.
My 05 Escalade had a Jasper rebuilt transmission in it when I bought it at 83K miles, I think it had only about 15K miles on it total when it started slipping again. The 4L60/700R4 variants were garbage stock. The problem was they were matched to an engine that was right at their torque handling limits. The 6.0L from that generation got the 4L65 where the 5.3L got the 4L60. GM seemed to build the 6 speed tougher from the get-go so they appear to me to experience less problems. In the earlier versions like what was in my first 96 Vette, the hi performance LT4 engine wasn't available with an automatic, the 4L60 couldn't handle the 360lb/ft that the engine made. If you got the standard LT1 engine (330 lb/ft IIRC) it was mated to an automatic. My first one was an automatic and the trans was starting to act up at 65K miles when I got rid of it and I didn't even drive it very hard.
I've known a few people with Escalades, Tahoes and Suburbans that had to have their transmissions rebuilt before 100K miles.
I'm a bit nervous about the EXT I picked up as it has 180K miles on it and surprisingly the transmission shifts smoothly and the previous owner (2nd) says he never had to replace the transmission in the 75K miles he'd owned it. If the tranny goes though I'll invest in a performance rebuild. I might even give it a go myself to see if I can do it.