I was replacing Lizzie’s Kingston carburetor with a new Holley NH as the old Kingston was flooding badly and I figured I would pull it out and rebuild it and in the meantime use the rebuilt NH and in the end I’d have a spare carburetor ready to go.
As I got the new carburetor in, I noticed the horn bracket was loose and I decided I would retorque the head bolts to 55ftlbs (I think I have a steel head even though it does not say Ford MADE IN USA on it because it’s magnetized). Most were all up to snuff at about 55ftlbs.
Then I got to the center bolt just ahead of #4 plug, and it was only snugging to a point then becoming loose again. I snugged it down as much as it would go (about 25ftlbs) and I started the engine to see if the mixture was good. Oil began gurgling out of the bolt and I shut the engine down (it only ran for about 15 seconds). I began unscrewing the bolt while praying that it wasn’t cracked inside the block.
Turns out the bolt came out in one piece and the bottom most threads are all totally stripped. I’m going to pull the head off the engine tomorrow afternoon after work to see what’s going on inside the back two cylinders and see if the top of my block is good (hopefully it doesn’t need to be milled).
It looks like the bolts are missing some threads compared to pictures I see of other T head bolts, maybe it is cracked deep inside the head after all.

How do I measure the bolt to see if it’s missing the bottom?
How do I determine what bolts I need? Seems like there are different bolts for different heads.
Are the bolts supposed to bottom out?
How do I determine if I need to retap the block threads?
What thread tap and drill should I use to retap the block threads (if necessary)?
What should I do immediately to prevent any further damage to the engine? (Remove head, oil, and coolant?)
Here is a link with pictures of the stripped bolt. I’m not sure if it’s cracked. https://imgur.com/a/G0omH3a
How should I proceed?