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You have to remove the oil pan. It is different for 2wheel drive and 4 wheel drive. In either case, you have to jack up and support the engine. Most of the time you must also remove the transmission rear mount so you can jack up the transmission also in order to get enough clearance to get the pan out between the transmission bell housing and the frame crossmember.
On 4X4 vehicles, you must also first remove the skid plates and the front drive axle to get the oil pan off.
there are 2 systems.
one is a part time system only.the 4x4 locks and is for ice mud and snow.Driving full time will damage the transfer case.The other system is a full time system and the selector says 2wd,4wd part time ,4wd full time and 4 lo. if in full time,it can be driven all the time even on dry roads.The full time is really an all wheel drive system.
the 4low is a very low gear and the main shifter has to be put in neutral and then the transfer case put in 4 low.attempting to put it in 4 low while in "drive" will make a gear grinding noise.
getting out of 4 low is the opposite.shifter to neutral and then put it in 2wd and then in drive.The newer durango has an electronic transfer case with a dial on the dash.The 2002 was available with 2wd,4wd,awd and 4 lo on a switch.The 1999 has the lever on the floor .
Wheel bearing should be permant packed. However if you wish to tackle the job. Remove the wheel, remove the cap, remove the carter pin, remove the bearings. Clean, repack new bearings and reasemble. But, before you do check with any auto repair shop or Dodge dealer, bearings may be permantly sealed.
It's a big job. Drain the coolant down, recover the freon in the ac system and disconnect the lines and heater hoses. Lower the steering column, remove the instrument panel assembly, remove the heater housing. Split the case halves on the housing and there you are. Usually around 500 to 700 dollars at a dealership.
I have a 99 dodge 1500 that had the exact same problem. It was the speed sensor on the rear end mounted on the top side near the pinion gear. It is an easy repacement part. After removing the retainer and wire clip it pulls out.