I wound up going with 1950 Chrysler 250 CI pistons in 0.080 oversize (about 0.015 oversize of the 216 bore) with the 235 crankshaft and rods in my 216. I had a machine shop bore the block to fit the pistons and it cleaned up nicely, being standard bore. They also narrowed the #3 bearing journal to fit later 235 main bearings and bored the rear main journal area for a full circle seal. The also ground the 235 crank to 0.020 undersize.

I've gotten the main bearings fitted to the crank (took a few shims to get the clearance right), and today tried fitting a piston. The good news is that the piston crown sits about 0.020 proud of the deck, and the head gasket is 0.079 thick. Allowing for a little compression of the gasket, the pistons should clear the head without issue. The bad news is the skirt of the pistons is just a bit too long to clear the crank counterweights at the bottom of the stroke, so I'll hit up a friend with a lathe to trim the piston skirts down a touch so that the crank will go all the way around. I think I lucked out on which cylinder I picked as some of the cylinders have more clearance to the crank. It would have been bad to get them all in with rings, etc. and then find out the crank wouldn't turn. The 216 pistons have slipper style skirts, but the Chrysler pistons are full skirt like the 235 pistons are. I'll trim them to the same length as the 235 piston skirts to be sure they clear.

So the engine assembly is on hold for a bit until I get the pistons trimmed up.
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Kevin
1951 Chevy 3100 work truck
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1929 Ford pickup restored from the ground up. | 1929 Ford Special Coupe (First car)
Busting rust since the mid-60's
If you're smart enough to take it apart, you darn well better be smart enough to put it back together.