I've got a 53 with a straight 8 and I had mine rebuilt because I'm keeping the car as close to original as possible. The motor has been bored .040 over with all the associated crank changes. Most internals were reused. I had to rebuild mine because the rings were sealed to the pistons and had very very low compression.
All that remains is painting the motor and bay and getting it back in and the car will be back on the road.
Rebuild took 16 months, but straight 8 rebuilders are not on every corner, most have never seen one.
Several conditions should be taken into consideration about what you want to do. Are you keeping the car? If yes, then keep the straight 8 until it dies then put in a crate or alternate. If you plan on selling it as an original, keep the 8. If you're rodding it, change the motor when the 8 goes out.
edit after seeing the car: Keep the straight 8 and keep it original...beautiful car (but I'm partial to early 50's Pontiacs)
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53 Chieftain "Herman"
55 wagon
72 Grandville
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