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I love four speeds especially in A-bodies but in heavy traffic such as the Woodward Dream Cruise an automatic is great.

I'm thinking valve stem seals. With the right tools These can be replaced by removing the valve covers & valve springs. As others stated it could be more significant like worn rings & would need a rebuild.

Might have 8 3/4 with a V8, most probably had 7 1/4.

Looks like there consensus that there's something wrong. I would step back & first determine if it's low engine output or something downstream in the driveline. So first I would check engine stuff like getting full throttle, fuel filter, ignition timing, exhaust back pressure, clean air...

I think that a Prowler transaxle would be pretty cool in an A body. Might be able to move engine a little bit rearward too.

Why not paint it with "cast iron" paint, it'll look factory fresh.