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I had the heads off my '68 440 a couple of years ago. At that time, I replaced the factory steel shim head gaskets with thicker Felpro's. I could feel no difference in performance: my car is mainly a highway cruiser, and I don't race it. I can run 91 octane in it, with no detonation.
I had Dwayne (PRHeads) brush up a set that I'm going to put on a 72 440 with a comp 501/510 solid and a gear vendor OD and 4.10's. I expect it'll run ok.
I did my 65 from manual to power. I used the column out of a 64 sport fury. My car is a 4speed. I sent the pump out
for rebuild and bought a rebuilt box from an auto parts chain. Everything fits and work good with no leaks.
But I STRONGLY recommend getting an aftermarket performance steering...
What year 440, 1967? If so I wouldn’t bother switching cylinder heads. As fat as camshaft I would contact a grinder like Jones Cams and ask for a custom grind.