Don’t bother with the 6L90. It’s hard to beat a 4L80 for comfort, durability, and ease of use. Gear the differential so at 65-70 mph the engine is starting to come onto its torque curve
Go with the big block. And since torque is the name of the game here, don’t limit yourself to big block Chevy. A 455 Buick or olds swap, or even a 500 Cadillac is a fairly easy project. Before I had my diesel Ram, I used my dads 455 olds swapped 81 GMC to haul my car to the various races. It’s a basically stock 71 455, the truck has 3.08 gears and the trailer loaded weighs around 6500-7k. It has zero problem pulling the trailer and interstate speeds.
Diesels are hard to beat, but with the cost of diesel fuel the added fuel economy isn’t nearly the advantage it use to be.
All Q-Jets are capable of at least 750 cfm. The small block carb will need some calibration changes for the bigger engine. Get with a Q-Jet specialist, they can provide the expertise and parts to get the carb right.