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Sounds like the first order of business will be to pull the pan, look for clutch or metal in the fluid, inspect the filter, check snugness of valve body fasteners.
I agree: I used to run those heavy slugs and then try to rev it to the moon. The engines started to last after I got smart and started lightening them. These days just buy the lighter pistons.
440. They're both old and chances of either running like new is low. Go to Summit and you can order 440 pistons to your door in a day most likely and it will feel 27 better believe it or not. Besides a 66 block in a 66, it's magic.
Not many people restoring swing fender or other classic Dodge trucks. I would scrap most of that stuff too to avoid tripping on it for the next 30 or 40 years.
I've swapped them before and I didn't notice any earth shattering difference. I never got a smaller one to stall higher than 2000 either. I think other than a big C-body with tall gears I would use the smaller one given the choice.
Not worth effing with it IMO. Think how that narrow bore is going to work with valves that open near the edge of 4.25 bore. Just spend a bit more and get a normal block that doesn't require custom parts. The Pro Stockers used destrokers not small pistons, just wouldn't make any sense.