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I had a 1991 Dodge 2 wheel drive with the intercooled Cummins 5.9 and the 4 speed automatic. Never had a bit of trouble with the engine but the transmission was the weak link. It finally failed at around 125k and I traded the truck on a new 1999 Ford Super Duty. The transmission was always a problem.
If you intend to use your truck for heavy towing you do not want that 1991 Dodge. The problem was that the Cummins engine had far too much torque for the transmission to handle. To keep the torque from destroying the transmission Chrysler put a high slip torque converter on the front of their old 727 design transmission. It worked fine while you were moving down the road but if you stopped on a hill with a heavy trailer you could not get it moving. The converter would slip so much that you could floor it and it would just sit there. I ended up backing down hills plenty of times and then getting a run for it, hoping I would not have to stop for a traffic signal, etc. My brother-in-law had a 1993 4 wheel drive that did exactly the same thing. We had a mutual friend that managed a Dodge dealership who told us every one of these trucks they ever sold to someone who towed heavy had the same problem. Chrysler finally came out with a newer design transmission that could stand more torque. My brother-in-law traded his on a 1996 that performed much better.