I was working on my brakes and pulled my drum off and was greeted with this pleasant sight... What is wrong? I've looked around the site for pictures, and I haven't seen any like this

 

That wheel cylinder and seal combined look pretty hurt.
I would change everything.. Wheel cylinder, Shoe's, Hardware,Self aduster's, Seal's. while your at it check the steel lines on the axle. In some area's they rust and break during servicing.

 

Btw I'd put a jack stand under that axle. Don't rely on just a floor jack.

 

WOW! That is pretty bad looking. I does look like the seals on the wheel cylinder went.

 

I would be doing this in the parking lot of my apartment building, and that makes a whole lot of things more difficult... How hard is it to change all of that? Should I also doing the bearing while I'm in there?

 

You don't need to do a bearing if it isn't bad. As far as the seal job, it isn't too bad to do. You will need to remove the differential cover and remove the center pin bolt along with the center pin in the carrier. Be careful after pulling the pin, if you need to spin the carrier at all take caution not to drop the spider gears out. To remove the axle to get to the seal you will need to push the axle in just a hair and remove the c-clip holding the axle in the carrier in the differential housing. Once the c-clip is out pull the axle out and remove your seal. Reverse procedure for installation. And then finish up doing your brakes and wheel cylinders! As long as you do have the differential cover off, you might as well do both wheel seals.... just a little preventative maintenance.

 

The 8.25 is a C-clip axle? I remember something about there being different kinds? Or is it just held on by a cap/plate at the wheel?
This is pretty far out of my normal stuff. The craziest I've done with the Jeep is motor mounts and brackets, and ball joints in the front.

Also, how much in/out play should an axle have? Mine "clicks" and has motion I can feel when I jack the back wheels up and push/pull on them.

 

Bumping this up for comments. I filled up my front differential and the next morning, I had the oil on the driveway so I'm thinking my seal is gone too. I have to do the brakes as well so if it's not too much work, I'll do it. Wouldn't you do the bearings too if you have the axle shafts out?

 

Front axle is a whole different beast than the back axle, that little bit I do know.

 

I usually leave diff. bearings alone unless they are known bad. However if you'd like to change them there's certainly no harm in doing so. Just don't use the cheap Chinese bearings. Get NSK, SKF, etc.

 

Disc Brake Conversion ftw!

 

I would if I had the money...

 

Where do I find those? All I've found are Chinese ones, or Timken.