I've got a '95 1500 with the 5.9 and 103K miles. The trans sometimes hangs up in 2nd gear and you have to let off on the gas for a moment and then it will upshift into 3rd. I've heard that is a common problem. This is the only trans trouble I have had in 12 years.
That's because the lining on the band is pretty-well GONE. Expect to replace the drum when you get your tranny rebuilt. (This was my experience, anyway.)
I have a 99 with a 5.2, two wheel drive. You WILL need the tranny rebuilt around 100K miles. Mine had 106 and I'd hoped the previous owner had done it. Nope. $1800 later, she's good for another 80-100K.
You'll be paying someone to r&r the heater core, too. Mine's leaking enough to give me a sinus infection. The whole dash has to come out to do the job.
Don't get me wrong, I LOVE this vehicle, but the trannies are pretty lame. A friend of mine with a 96 4WD went through 4 of them in his.