Always manually adjust the rear shoes up.

Bled everything again last night, including master cylinder. I was thinking.... swap master cylinder today and two new calipers and pads up front. I did not see a leak last night but the flow out of the LF caliper and LR drum are weak. If that doesn't work.... I will just get steel lines from rough country and a brake booster and that should work. I will have to watch some you tube videos on drum brake since I have never messed with them before. I also thought about plugging the rear brakes and just going off front brakes. Not sure how well the stopping power will be, but it's just a woods jeep and I don't drive on highway to often.

First thing brakes on XJs from 96 down have never been worth a C R A P... Blocking off rears will make it even worse. Just adjust backs up and bleed best its gonna get. Upgrdaeing to 96 or newer booster will definitely be a big help if ya wanna go that far. This video shows how simple adjusting rears are. If your gonna pull the drums put new shoes on at leas.....

I generally bench bleed right on the vehicle with everything hooked up. Faster, less mess, and I usually get no air in the system so bleeding is optional.

After you bench bleed it off the car some air can get into the master when hooking up the lines. Since the Cherokee's cylinder is at an angle you can wind up with some air trapped in it. Raise the rear or lower the front to get the master at least level, rear higher will be fine too. This will put the ports at the highest point allowing air to bubble up into the reservoir. Once there's absolutely no bubbling then bleed the system and you should be fine.

Update:
Got a new master cylinder, front calipers, and front pads. Felt like the brakes were starting to comes back until I felt a give and they went back to the floor. The back rear brake line blew out, got a new line ordered this morning and will replace the rear drum brakes also. The parts house says there are 3 different lengths on the rear drums brakes, is there a way to know without tearing the brakes down? Thanks for all the help so far, finally making some progress.

Ive had the same problem on a few of my XJs in the past. On mine, it was a combination of excessive wear on the drums and the shoes. The lining of the drums gets beyond its wear limit, and the shoes get worn down. Replace the drums and the rear shoes, and make sure the rear shoes are adjusted properly. Should make a world of difference.

Did not even consider the drums! I'll get those and some pads and see what happens! Thanks.

The rear brake line popped, it was probably why you were getting a mushy pedal. Once it's replaced you'll probably be fine. I'd suggest checking the rear brakes before just ordering parts, they may need nothing or may need everything.

Should replace the front hoses also.

I get the rear lines this Friday, I will give a update once I get a chance to work on everything. But I will tear the rear apart and assess the situation for sure.

Update:

New front caliper and shoes/new master cylinder. Booster appears good, no change in idle with braking or spraying it down with brake cleaner. New rear brake line installed. Had to adjust the rear drum brakes, the braking is much better but still doesn't stop on a dime, but overall stops good enough for a woods truck. I'm going to replace the rear shoes (about 25-35% life left) and replace one of the rear drum tension springs (sticks a little after adjusting). Hopefully changing the shoes will make the stopping power better. But if someone slammed on brakes in front of me and I was riding their *** or not paying attention it would be a close call. From what I hear these brakes are not the best and should be up graded. I have about $900 invested in the jeep and parts, hopefully I can get a couple years out of it with 218K miles on it. Thanks for all the help!