I'd be curious to hear more about this also. My 58 has a similar oil line going to the head based on your description. I remember reading something somewhere about a head bolt that blocks an oil passage if a certain mismatched year of head and block are used together. The correct head bolt to use has a grove that allows oil to get to the head and if the wrong one is used it blocks that passage. So I was thinking maybe on my setup and perhaps other peoples, a previous owner did this bypass oil line to "fix" the mix match head/block no oil thing. I have not gotten around to figuring that out yet on my truck. I'd like to hear what those who know have to say.