IF it needs major engine work in the near future a swap to a slightly newer engine should be easier to get rebuild parts for.
A '55 272 or 292 can appear virtually the same as the original 239 if that's a concern.
Fyi, some of the early 239 Y-block engine parts (cam bearings for example) aren't available or interchangeable with other years like the 272 and later versions made thru '64.
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You memory of the cam / dist tooth count is correct. And the shaft hardware just below it to drive the oil pump was different also. Not the more common hex drive....
The earlier engine had a different number of gear teeth on the cam for the distributor ( I want to say 13 instead of 14...going off of memory.) ...
Was told by Victor at Red,s headers that they fit 54 car only.
I think it has to do with the length of the pipe coming out of the common rail, that makes it 54 only.