I don't have a stall yet. That's next on the mod list. Going to do a 3000 or whatever Davenport recommends. My cam wakes up at 2500 and pulls like stink until shifting at 6100. Trans is stock except the thermal bypass valve. I was running the pill flip until yesterday, then I bought the updated GM part that opens at a lower temp. Lots of info on this site about that mod.
8L90's will take more than 600. There isn't much good info about our trucks online, but I go on the Camaro/Corvette forums to look for mods and info. Any Camaro/Corvette with an "A8" is the exact transmission the trucks get, the 8L90. Their engine is called LT1 but it is 95% the same as the L86. Most mods for them work for us.
I know what you mean about the "holding the gear" thing. My truck did the same thing stock. It's a dumb fuel saving algorithm in the tranny's programming. It's trying not to downshift to save gas, until you floor it then the trans goes "OK! you want it, you got it". There is also flex in the gas pedal. Earlier trucks, like yours, are made of flimsy plastic that actually move when you push the pedal. So when you are pushing the pedal down the throttle position doesn't change as much as it should. There are fixes on here like the "paint stick mod" or you can get the newer pedal. When you get a proper tune most of that lag will go away when they adjust the throttle response and fine tune the tranny for performance.
My mistake about Blackbear. Last time I checked EFI Live didn't support the 8L90. They must have added that. I know of a couple guys with Player3 tunes in their Gen 5 trucks. They are from Edmonton and I have heard good things.
I will highly recommend Davenport. They did my cam and tuning, and I will be going back for a converter this year. They are one of the best in Canada, if not the best, at modifying and tuning late model GM products. They specialize in Camaros and Corvettes, but, our trucks are almost exactly the same.