Quite honestly, the truck you're looking at is a cruiser and a tow rig. The most mods that I would do to it is straight pipe it, air filter kit, boost, pyro and trans temp gauges. It'll run forever at stock power levels.
The automatic in the first gens aren't that bad, as long as you leave it alone. It's been awhile since I've been around one, but if it's possible, turn the OD off when towing and pulling grades.
The values of 1st gen Cummins trucks are all over the place. It really depends where the truck is located. All diesels sell for more than KBB value in KY, IN and OH.
If the truck you're looking at is 2WD, and in good shape, anywhere from $3k to $5k. If it's a 4WD it could be sold for as much as $10k.
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