I have a 98 2500, with the early 14 valve diesel engine. Engine is great except the fuel millage sucks compared to the old 12 valve motor, but it does have more power (it"s stock). Eugine wise i wouldn"t be too worried about a chip or bigger injectors/turbo... they"re not quite bullet proof, but close, if the power is kept reasonable... more worried about who/how it was driven. We have 260k miles on ours now, and the bodywork is starting to give up, the box especially...
My worry over extra power is the transmission, 5th gear is known for being bad if it pulls lots and heavy loads... and if it"s an auto, i"d want a big cooler. We"ve gone through two transfer cases on ours so far... The absolute worst problem we have with the diesel is the front end parts... we go through the steering every couple of years... it"s not quite man enough for the heavy engine somehow... you will know when it needs done... steering will have no feel, half a turn or more before the wheels start to turn.
If your truck is in good shape, you might be better of to fix the motor then chip your truck to get more power... it would be cheaper than another truck... and you already know what you have.
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