First of all, that is a cool story, 57 year old one family car. Secondly, the fact that a Pontiac bottom end went 250k, assuming untouched, is pretty gnarly. I'm curious, tho, why the heads got replaced, and what they got replaced with. Sounds like a car that was well taken care of.
As much as I hate to give up on a 350, if you aren't concerned about originality, a crate 400 makes sense. It would look the same externally. And it depends on how much DIY skill and desire you have.
How badly the power bug bites you will also play a fun game of finding the next weakest link, especially with the easy power with bigger cubes.
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"...ridge reamer and ring compressor? Do they have tools like that?"
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