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The nut looks to be a friction locking nut, if so cotter pin not reqd.

Yup, Something is bent or faulty. Could be from previous collision damage. Not much point replacing anything until you determine what is at fault....& fix that first.

Both leaf & coil springs can be 're-set' at a spring shop. No need to but new springs.

It ain't broke, why change it?

Have you tried Summit? Brake shoes. Brake drums of this size can generally be safely machined 0.060" to fix ovality/scoring etc. Generic brake shoes are probably made to stock size, not an oversize drum. The shoes may need to be radius ground to the size of the drum; then they will 'work'.

If you are going to keep the car for many years, have your existing wheel cyls & M/c either brass or s/steel lined. No more rust problems.

Make sure the check valve [ booster body, where hose attaches ] is working.

[1] Pinhole [ or any hole ] in a booster diaphragm causes a hard pedal, not a mushy pedal because brake assist is lost. [2] Vac canister caused more mushy feel because the stored vacuum allowed greater braking force, pedal goes further. [3] Your problem is hydraulic. Either air in the system or...

What is your definition of 'high performance' ? - quickest stopping distance - longest life - least fade resistance

No, NOT lightweight springs. If you are going to use VA connected to manifold vacuum [ a veeeeeeeeeeeeeeeery good idea ], then you will have a lot of timing at cruise & lower rpms. If you put light springs in the HEI, you will probably have too much total timing. This may cause detonation. Total...

Vacuum canisters do not add vacuum, they just give more 'reserve' so that you get more than one pump of the pedal before you run out of brakes. If this is a low compression engine, then I can understand poor/no brakes with the 284 cam in a 360. Will not be much better with a high comp 360.

Cast iron M/cls are notorious for rusting & then they fail to seal properly, seals get damaged from riding over pitted rust. Hence a good move to have the m/cl lined with non-rusting metal.

I think you have answered most of your own questions. Pedal shudder during brake application is usually warped discs or out of round drums. Hissing booster has an air leak, needs fixing/replacing. You can have your m/c re-sleeved with s/steel or brass. Then fit new seals.

You have air in the system. Engine running, extra force provided by booster is compressing the air, lowering the pedal.

Post #5. What thrust angle? And why does he need more caster when we do not know what the current caster is? Some cars are limited by design as to how much more caster they can take. Caster moves the wheel backwards. Depending on the wheel opening, wheel diam & wheel offset with wide wheels...

Because of the high line pressure reqd with disc brakes, it always surprised me that street driven cars could be sold with un-boosted brakes. An accident waiting to happen...

Post #41. The travel of the MC p'rod will be the same if you move it up to the 'manual' hole position. The pedal travel will now be more, not less.

So, what exactly is the problem?

Probably an earlier set of brake shoes wore down to the rivets, which gouged the drum. Here, we only use bonded [ glued ] shoes, have done for decades...& this doesn't happen.

Have you measured the thickness of the individual leaves? That is needed to compare spring packs.