Good question and smart of you to be open to all options. First off, the difference between a total cut rate and maybe questionable trans rebuild would be -$1.5k. So figure you’re looking at that dollar amount up in the air after you take all your time to fix it.
With GM fighting for the strike of their life, it’s probably not a good time to upgrade as the parts warehouses are on strike too. The one in San Diego just went to 24/7 picket lines.
You could make good resale on selling private party as well as a trade, but keep in mind, unless you got a smoking deal on your 1st pick, hope too, always wanted truck, you’d still lose a little equity because new / used vehicle sales are high right now.
When our trans was hinting with a very occasional 2-3 slip on our 08 YXL Denali, we did find our dream truck at a TX Lexus Dlr and drove it back to CA. It gave us time to have a dealership pro Resto the paint & interior and sell it for $1.5k less that what we got our 09 Esky Plat ESV AWD for.
Three years after owning the Esky, the trans went out. I couldn’t be happier because I fully intended on keeping the truck. If you find your dream truck, buy it outright and then sell / fix the Burb when all the pressure’s off.
Do both. Shop for a trans rebuild as well as your dream truck. Keep in mind your Burb is likely due for the items I listed in another thread that are about 1-$1.5k if you buy them off R/A and have the shop install ur parts. Those same parts are 2-3x more in labor and cost is the shop sources them and the trans is not out.
I spent $6.5k for a hand rebuilt trans and all those parts, so I’m good from the 175k I’m at now til 275k clicks later.