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Is a late 440 worth it for a cruiser?

Forget the 440. Change the valve seals and the oil and drive it. If it doesn’t clear up then Re-ring the 413 and do the heads. You don’t need new pistons on and 83k mile engine.
I did this in 1992 with the 1962 Imperial I used as a daily driver in that era. Car ran perfectly for another 90,000 miles. I used to drive it from Chicago to the Chrysler Nationals in Carlisle every year.
 
Original heads will not have hardened valve seats either. For longevity, using lead additive would be recommended. If I read it right, you are in Cali, not sure if lead additive is even legal there.
 
I would not worry much about the heads, but the exhaust valves would like a little lead additive. If you want a bit more power, a valve job with the larger 1.74 exhaust valves would be very noticeable.
 
I'd add a couple degrees of timing to make it easier to start, along with what the others have said.
 
One thing is that a PCV valve was an option in 1962. So put one on if there is not one on it now.

A 1962 413 is a regular engine, nothing special inside. Small AFB, small cam, 1.60 exhaust valves, stamped steel rockers, log exhaust manifolds, 12” converter.

They do have good throttle response and bottom end torque so they are very responsive and peppy, nice to drive.

I wouldn’t change the exhaust valves, it’s all about the combination.
 
My machinist says that the Mopar engine blocks are hard. The metal is durable and long lasting. I’ve had a few 440 blocks that didn’t need to be bored, just honed to clean them up.
If you do pull the 413, it may be “reconditioned” just by honing the cylinders and replacing the rings, bearings and gaskets.
 
Installing one of these on the 413 would be the Bee's knees.
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To make it really fun, valve job with a deep cut, 1.74 exhaust valves, Maybe an RV style cam. The late '60's HP exhaust manifolds are good. Looks like a real fun project. A '62 300 is amazing. Enjoy.
 
To make it really fun, valve job with a deep cut, 1.74 exhaust valves, Maybe an RV style cam. The late '60's HP exhaust manifolds are good. Looks like a real fun project. A '62 300 is amazing. Enjoy.

Thanks! Speaking of cams, I’ve been eyeballing the Summit 6401 cam. Wondering if it might be worth it to install on the 413. Not a high performance cam, just a mild one slightly above stock. I believe you can even reuse stock springs. Here’s a ‘66 Charger running the 6401 cam in its 440!

 
Cam selection is a very tricky deal. I would call a few of the name company's and ask about RV cams. My experience is from 40 years ago, but I put a Comp RV cam in my 360 van tow vehicle, 4700# plus the 5700# trailer. The Comp HE cam had great torque and amazingly good gas mileage. Check several brands.
 
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