Brakes won't bleed! Master Cylinder Gasket???

Could this shitted up flare have been to blame for the leaking master and air getting into the system?

 

Dick,
I've done all of that that matters. Drums have been adjusted. Truck is high enough that it doesn't need jack stands, I've started at furthest away. When that didn't work, since the front/rear are separate, it shouldn't matter that I did the fronts out of order, right? Since I don't have a helper, I'm using one of the vacuum brake bleeders. I'm not pumping the PEDAL, I'm pumping the vacuum pump, at least when bleeding. I'm building the vacuum, cracking the bleeder, and watching the 3" piece of clear tubing for air bubbles. They don't stop, so I shouldn't move to the next wheel.

Maybe I should try jacking the rear and have someone turn the wheels to see if the brakes are stopping them from turning, though. Maybe the pedal feel I'm used to has been lost in the swap.

 

That flare could have something to do with it.....how is the seat the flare corresponds with?

 

That fitting looks jacked up for sure. Did that fix your problem?
Sometimes it helps to adjust the drum brakes up all the way so there is no movement in the wheel clinders bleed and then set the adjustment on the rear shoes.

 

When you use one of those bleeder set ups you need to pull it off of the bleeder on the vacuum stroke and let the bleeder start dripping for about 20 seconds, before you tighten it up. Air bubbles are common in the clear tube, however you shouldn't see them coming out of the bleeder, its due to the seal around the bleeder not being tight, and it will still work that way.