@Schurkey I know you hate the trailing drums on the JB5, why is that?
1. 10" drums are weak. Also, have little mass, get hot, fade.
2. The front shoe on each side wears faster than the rear shoe. Front shoe does almost all the "work" of braking.
3. The self-adjuster doesn't work unless you use the park brake frequently. The rear brakes are therefore almost always out-of-adjustment because nobody uses the park brake.
I've got a blown wheel cylinder and need to replace it asap but I was wondering if I should stop here and upgrade first.
Ideally, you'd upgrade. The 254mm (10") leading-trailing drums aren't worth putting money into.
Problem is, backing plates to put bigger brakes on the 10-bolt axle are tough to come by. Essentially, you'd need to swap the entire axle for a 14-bolt semi-float 9.5" ring-gear axle assembly, which also gets you the wonderful 11.x Duo-Servo drums.
The JB5 booster/master, and front rotors/calipers, combined with the 11.x rear brakes, is essentially JB6-equivalent.