Wondering if anyone can tell me what I need to do to drill a pilot bushing

What do you have in the back of the crank already? Just a center?
upload_2019-6-27_8-15-15.png
Then you should probably pull the crank if you want to get it to stock bore and depth dimensions. Check the oil passage locations and make sure you don't go too deep or too big in diameter. You should probably check the crank thrust bearing for wear and end play anyway.

If by chance it's drilled for adequate depth like this '68 440 steel auto crank and not diameter you could just do a self made bushing in the converter register as YR indicates and not cut the input. I don't think they are being made these days. Then too, you may even be able to open up that first step to accept the stock bushing.

upload_2019-6-27_8-17-26.png

Just a center in the crank and using a converter register bearing or bushing, measure for .100"/.125" clearance and trim the input.

Any way you go, indicate the bell housing in.