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You're talking about two different critters there, super cab vs reg cab, and the super cab is more than twice the price of the reg cab you're looking at.
I prefer the super cabs myself, I like to have the room to pack my gear out of the way and still be able to haul a passenger.
But both of those have the E4OD which is a deal breaker for me. Been there, won't go there again.
2 wheel drive vs. 4x4 also..., personally, for what I need a truck for, I will never buy a 2x4 ever again, and I would try to hold out for a D60 F350 instead of a TTB, but thats just me. For what it is the brick nose is priced too steep. My advice would be to keep looking ...
I would choose the 91 over the 92, even though it is an extended cab and I prefer regular cabs.
However, the 91 with a fresh coat of paint might be hiding other issues, like rust in the cab.
Anyone's guess what "needs work" means, and it probably has icky auto transmission, but the drivetrain can be remedied and for 1,800$ a nice, clean straight bodied f350 4x4 crew cab diesel VIN truck is a great starting point. Just need to buy a western truck like this for the body, and a rusted out eastern truck with a good engine and ZF to swap in, and your good!
Rezvani's Latest Post-Apocalyptic Monster Is a Ford F-150 Raptor Underneath
Slideshow: Called the Fortress, the 850-horsepower pickup combines Raptor underpinnings with military-inspired features, survival equipment, and a starting price of $285,000.