The end of your dizzy shaft does not appeared sheared off like your mechanic suggested. But comparing it to your second dizzy would confirm that. I do think I see some extra wear at the very tip about 1/16" of it.
I'm thinking, or just guessing, that maybe,,, the dizzy was inserted in as far as it would go but not into the oil pump slot. Then the clamp was tightened around the dizzy shaft but the clamp wasn't absolutely down hard to the block. Then when the clamp was bolted down tight to the block, the dizzy shaft had pressure pushing down on the pump but not inserted into it. When the engine was cranked, the dizzy shaft entered the pump slot just a tad and just enough to turn the pump producing oil pressure. The slight tip into the pump only lasted so long and with a little bit of wear finally worked free of the pump slot and no more oil pressure.
Just a theory but it could explain having oil pressure for a little while.