Sounds like some good projects. Were I to do it over again I'd likely go for the 3/4 ton with the 4L80E. I'm not having trouble with my Sub (yet), but I'm intendign to haul a pop-up camper trailer up and down CA in the coming year and I'm concerned it might be the death knell for my trans.
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yesterday / today I finally got around to doing the oil pan gasket change on my Sub. Same project as on the Tahoe. Somehow it went slower this time, instead of faster.
/Suburban/oilpan02_zpsht29frvp.jpg
Looking at the flywheel and no signs of rear main seal leakage. 128k mi and 14yrs, not bad.
Cylinders #5 & 6, showing some scoring. Nowhere near as smooth and shiny as the missus' '05 Tahoe bores were, with 50k more miles. IIRC they're both LM7 motors. Non flex fuel. I wonder if there was a bore tech change in the later half of the model series. '03-'06.
Looking forward at the re-installed windage tray and oil pump pickup, over the unbolted / dropped axle. Have to drop it down to get the pan out. I changed the o-ring on the p/u tube while I had things apart.
Late ETA - while you have the pan off, change your oil cooler gasket (adjacent to the oil filter mount location). You can do it on the vehicle, it's accessible with the front driveshaft and exhaust downpipe in the foreground, but it would be a lot easier to change it while the pan is off the vehicle.
Now I get about a half-day's rest before tearing the front off my neighbor's '03 Tundra 4.7L DOHC V-8 to replace its timing belt, pulleys, water pump.