could be shoes way out of adjustment but could also be a failing master. When a master is leaking a bit internally you can sometimes get a little more clamping action by pumping the pedal and moving the air bubbles in the line around. Sounds like you need a better mechanic. I'd start by having a look at the fluid level in the master cylinder bowls. Also look at the backing plates of each drum for any sign of leakage at the bottom of the drums as well as anywhere else along the brakelines for dripping or even wet spots indicating tiny leaks especially at fitting locations.
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My Break Away Squad
1969 Fbird (Base, 350 & Sprint Cvt’s - 400HO & TA Hardtops)
1969 LeMans (2dr & 4dr Hardtop and a Cvt)
1969 LeMans Safari 2 seat Wagon
1969 GTO (2 Cvt, 2 Hardtops & Judge Hardtop)
1969 Catalina (3 Cvt’s & a 2dr hardtop)
1969 Ventura 2 Seat Wagon
1969 Executive 4dr Sedan
1969 Bonnie Cvt
1969 Bonnie 3 Seat Wagon (2 of them)
1969 Bonnie Brougham (4dr Hardtop & Cvt)
1969 Grand Prix SJ (2 of them)
1969 2+2 2dr Hardtop (Canadian model)
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