Why would I have coolant and oil puddled up in this hole?

There's a shaft in this hole that I am assuming is the oil return?

Here's some relevant info:
d16z6
built last year, didnt leak oil or coolant before I pulled the motor.
arp headstuds
oe headgasket
felpro intake gasket



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Check your VC gasket.

 

Wont leak coolant, just oil. I'd say you've got a leaky intake manifold gasket.

 

I know there are oil/coolant passages on the distributor side, are there passages in this spot too?

 

No, just one coolant passage on the distributor side as I recall, but it might be running along and leaking there, it's either that or you've got an issue with the head itself.