Help me out with deciding on a tow rig...?
 

Not quite sure what direction I want to go here, I was originally thinking just get a 2002-2006 Escalade/Yukon Denali cuz it's comfy and has a lot of amenities and has more than enough towing capacity. Car and trailer should be about 5500lbs max, so since they tow 7500lbs - that's more than enough. And you can pick them up all day for $7-9k with 125-150k miles. I figured pull out the 3rd row seats and toss in a weather tech mat and my tools/jack/spares on top - should be fine...

However then the denmah mentioned that the Escalade will have a 4L60e-based (4L65) trans and honestly I agree that they aren't the best - And I'd be towing over the mountain passes (Which are no joke) in central WA/OR.

I balked that you can't find a 2500 truck for the same money and he said "You can't find a 2500 gasser for $10k??" - Which, you totally can... however they're just going to have a cloth interior and none of the luxury items really. Budget would be $8-14k

I admit It's likely easier to add the amenities I'd want to an HD pickup, than swap a 4l80 (or potentially another 4L65) into an Escalade

My range for models are 2000-2008ish Chevy/GMC 2500 crew cab, but not sure on if I want to do gas or diesel for the towing...

Items I definitely want are the following (most can be done aftermarket)...
-Crew cab/seating for 4 adults comfortably
-Power seats (heated would be nice but not necessary)
-Tilt/telescoping wheel
-4WD/AWD
-Single zone climate control (dual is fine but whatever)
-power windows and locks
-Bedliner (can do aftermarket)
-Tonneau cover (can do aftermarket)
-Android Auto (can do aftermarket)
-Rear view camera (can do aftermarket with radio)
-Keyless+Remote start (can do aftermarket)
-trailer brake controller (obviously - can also do aftermarket)


I would like it to feel powerful - I figure if the 6.0 gasser sucks I can either do a heads/cam swap and tune or just throw a blower on it honestly. But for the price you could get a diesel (even if higher miles in the 175-225k range), they're reliable with high miles right? How reliable are these 6.6 D-Maxes and the Allisons typically behind them? Do I really even need the diesel? Do I really even need a 6.0/4L80 or is a Yukon Denali/Escalade fine as long as I use good fluid and a cooler?

Thanks for reading all this shit :)