I'm thinking the rubber bushing can't be expanding the outer steel sleeve significantly (unless it's a split sleeve I suppose). So if I need to push the bushing out it seems like the best option would be to press the outer sleeve out and let the rubber bushing and inner sleeve come out with it.

But the rubber and inner sleeve both look pretty solid, so I'm thinking it wouldn't be bad just leaving it all in and reusing it.

 

I had to do both of my rear hangers this past winter. When I got my truck, the driver side hanger had let go and was rubbing the underside of the bed.

I figured if the hanger was that bad I should do the shackle/bushing too and IMO the bushing was the worst part. I had no choice about replacing the bushing or shackle because the bolts were rusted to the point that 3 days of PB blaster soakings wouldn't convince them to turn, so I cut the head and nut off.
For the bushings, I used a small drill bit to chew at the rubber part in several spots. Then I took a cutting wheel and slipped it in the seam(?) where the spring eye curls around to cut the metal sleeve of the bushing. This gave me a relief cut to help get the sleeve out of its home.

With caution, persistence, and a whole lot of hammering/sparks, I did both sides with the bed on in 2 days.
Good luck and be safe!

 

As it turned out, it took about a week and a half to change the driver's side, and then 3 hours to do the passenger side. Everything went about the same as the first, but I knew what to expect (and already had the air chisel).

I did end up leaving the old bushings in the spring eyes. There was no way I saw to get them out while the springs were in the truck, and like I said, they didn't look too bad.

I did replace both shackle bolts, the shackle and the spring hanger on both sides.

Thank to everyone for their suggestions.

 

You did put the spring/shackle bolt from the inside-out correct?

 

Yes, I put both bolts in the same way they were, the top (spring/shackle) from the inside out and the bottom (shackle/hanger) from the outside in. It seems like more of a pain that way because the frame gets in the way of installing / removing the top bolt, but it didn't look like there'd be clearance for the end of the bolt sticking out through the nut between the spring and frame.

 

Correct, not enough clearance. That is why they put them in that way. I am glad you did, it would suck to have to tear it apart again to flip them