5.8 rebuild or diesel swap?
How much time/money do you have? What are you looking to gain?
A diesel swap will cost significantly
more than refreshing the original drivetrain. The only real net positives are fuel mileage and torque, plus simplicity if you go for the Zombie Apocalypse proof all mechanical diesel.
I was thinking in this direction when I bought our '92, but the more I think about it the less sense it makes. Recent discussions here have been about LS swaps, and you can swap in an LS/modern trans/TC for about what a rebuilt and slightly upgraded 351 would cost (if you're doing the work). For a usable trail rig, this makes a LOT of sense (though putting a GM engine in a Bronco does hurt a bit).
rebuild *.8 or 9 in install?...TTB or SAS and how to do it ?
Again for a trail rig... cost vs. benefit... I'm still planning 3/4 ton axles and SAS eventually, but it's probably not necssary.
automatic to 5 speed?
Something else I originally thought about, but the auto is easier to drive off-road and in snow, especially for my wife. (See benefits of modern transmission with LS swap above...).