Cant measure crank ID for bushing, my calipers won’t reach past the ring
Had to drive new bushing in rather forcefully, seems that the trans
Wont go past bushing and allow me to bolt the motor up.
Had ti get the smaller fly wheel and now I think there must be something else i did wrong

Are you sure the old bushing wasn't still there when you pounded in the new one? The pilot bushing holes are the same on the small and large register cranks, I have heard but never experienced that some automatic cranks didn't have the pilot busing holes fully machined and need to be reamed out before the bushing can be set, maybe that is what happened and it made the bushing too tight. Did the crank work with a manual transmission before?

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If you didn't drive it there, it's not a street car.

then

I experienced that, I was able to press a bushing in, without a lot of difficulty, and even get the transmission installed.
problem was that the tranny pilot shaft was being driven when motor was started. Could not shift from neutral,

In my case I was working with a crank that was drilled for a manual tranny but did not have a bushing installed by the factory.
So in those cases be careful, the depth my be good but it may not have been reamed to size.
If you are working with a crank that has a bushing installed by the factory, it should be OK for depth and diameter.

to measure an inner diameter like the pilot bore on a crank use a telescoping micrometer

http://www.sharpfine.com/others/telescoping-gauge.html

you can get a set at HF that is functional, just be carefu and measure and re measure a couple of times till you get a feel for
the process.

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Doo Ron Ron and the Duke of Earl are friends of mine.....
https://www.youtube.com/watch?v=uX8Nj8ABEI8

NAPA has a bushing for the unfinished crank hole.

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Official Cookie and Mater Tormentor.

Last time I checked, a few years ago, they were discontinued. I had to take a standard bushing, and turn down the OD.

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Charrlie_S
65 Valiant 100 2dr post 170 turbo
66 Valiant Signet 225 nitrous
64 Valiant Signet
64 Valiant 4dr 170