Things Change.. Butters is now getting a 392

No Bolts Left Behind on YT had an issue with the oil pressure on his 5.7 swap and it turned out to be the wrong pickup. I guess the tab is clocked differently between a VVT motor and no-VVT motor and he had the wrong one so it didn't bolt down square and allowed for a leak. Based on your picture, doesn't look like that is your issue, but maybe the o-ring got kinked or cut during installation?
Yes, the vvt and non vvt is clocked different. Everything looked good when it went together and came apart with new o ring. I'll replace the oring this time as well. I've read threads on other forums of similar oil pressures. Actually seems pretty common... I just don't want to be thinking about it all the time.