I am in the process of swapping a 216 out of my 40 Chev. pu for a 1955 235 out of a 1T. I didn't plan on becoming an "expert" on flywheels, but I have learned a few things that might help others.
The '40 216 flywheel has a 2 1/4 bore and the mounting bolt holes are 3/8 dia. I have a '53 flywheel has a 2 1/16 bore and the mounting bolt holes are 7/16 dia. The '55 engine needs the larger bolt hole flywheel. Both have the 139 tooth ring. I also have a '59 235 out of a car. It has a 2 1/16 bore and 7/16 bolt holes. It has 169 teeth. The '59 clutch/pressure plate is 10" dia where the other 2 have 9 1/4" dia. This means the bolt pattern for the pressure plate assembly,on the 59 flywheel is different than the other 2 so the pressure plate/clutch will not interchange. In order to go to a newer 169 tooth flywheel you would need to go to a pressure plate/clutch to match that year. I have a T5 behind mine, so if I use the '53 flywheel I need the pressure plate out of my '40 and a clutch from an 84-84 Astro van (9"). If I were to use the '59 flywheel, I would need a '59 era pressure plate and a 84-85 Firebird V6 clutch (9 11/16"). I don't mean this information to sound like I am an expert, I'm just telling everyone what I have run into, so it might help them along the way.