RNichols,
Paid about $25K for my LB with 45K miles in mid-2000. It was a local gal's daily drive and never pulled, never hauled. Pretty straight other than a few door dings and minor paint blemishes.
In retrospect, I'd have preferred if it had towed some. The local Cummins shop said they need to be worked to be broken in right. Mine wasn't, really. The best mileage I've had, with modifications (exhaust, turbo, injectors, air intake, torque plate) is 16. 5 around town. I can live with that (but not as good as I was lead to expect from a friend with a '95).
Check steering/wander and brake pull. Check the front pads (they're cheap, but may explain pull, if any). Pull the rear wheels and the brake drums off and see if the axle seals are leaking (greasy brakes will tell). Look at the diff. at the U joint. Mine was greasy and needed a new seal a few months ago. If it still has stock batteries you may be in for new ones by now. Also, stock shocks? May be ready for new ones.
If it has an extended warranty with time/mileage left, see if you can assume it. I did for $50 and it has covered my axle and diff. seals.
What else, guys?
JK