Draining the trans on my 2000 is a little complicated. The drain plug is on the opposite side of the trans dip stick. You may take off the skid plate if you want. The plug actually is on the side of the case, so it may not drain straight down and get on the skid plate. This is from the manual:
1. Remove skid plate.
2. Place a drain pan beneath the transmission oil drain.
3. Loosen jam nut (A).
4. Turn adjuster bolt (B) in to allow removal of drain plug.
5. Remove drain plug and wipe the magnetic end clean to remove accumulated metal filings.
6. After the oil has drained completely, install a new sealing washer and install the drain plug. Torque to 14 ft. lbs. (1.93 kg-m).
7. Turn adjuster bolt (B) out until it touches the frame, and then and additional 1/2 turn.
8. Tighten the jam nut securely while holding the adjuster bolt.
9. Add the proper lubricant through the dipstick hole until the oil level is between the upper and lower limits., Do not overfill.
10. Check for leaks.
11. Reinstall skid plate if removed in step 1.

I know some of that is pretty basic, but wanted to give it to you just as it is in the manual. I'm trying to scan the picture and if it works will get that to you. It's not a very good picture in the manual. Normally I'd just take a picture of mine but it's covered in mud from the weekend.

 

Mark, check your PM.

 

Finally got it to scan right. Check your e-mail.