I re-did the driver side drum, and got everything put back together correctly. Working on bleeding them now. There must be a ton of air in the system, because maybe every 3rd time I open the bleeder, fluid with lots of air bubbles comes out. The rest of the time, it seems that nothing at all is coming out.

 

That's why I do the finger method on the first one. MUCH faster.

 

Yeah, I've been doing the finger method, sometimes I can feel the air against my finger, other times, nothing. I'm going to keep at it and hopefully I'll get a stream of clean fluid still.

 

Well, I got the brakes done yesterday. Bled everything, got nice clean fluid coming out, with no bubbles. Truck stops much nicer now, and the pedal feels much more firm.

Because the rear brake shoes were pretty much shot, with adjusters frozen, I'm not sure how much difference the 1-ton wheel cylinders made, vs just having new shoes and hardware back there. Either way, it's much better than before.

So in the few weeks since I've bought it, I've done

-rear brakes and cylinders
-power steering fluid
-plugs, wires, cap, rotor
-air filter
-oil changed
-pcv valve
-trans fluid
-t-case fluid
-both axles drained and re-filled

So I'm pretty much up to date with maintenance for a while.

Thank you to everyone for the help, and for putting up with me.