Leave it plugged in, you want all the oil going there that you can get.
Did you drill the case down from above in the cylinder area to intersect with the oil hole on that side?
The other thing you need to do is open up the hole out to the seal groove. The new bearing will cover up the hole so you need to groove it out so that the oil/mix can go down between the bearing and the seal. Also, when you put it together, there are little tabs on the seal, make sure you orient it so they don't block the oil groove.
I don't have any pictures, sorry.
sled_guy