I just dropped a 340 off to an engine builder who seems to be very familiar with this scenario.
I will get his take on this; I haven't thought of it until reading this. This engine will have Edelbrock heads with Harland Sharp rockers and head studs.
Could you use a head bolt in place of a stud at the oil passage?
My son did this 340 for a Demon with Edelbrock's . He put the recess in the studs. I am sure there are other ways to open this up. But the safest and easiest is to groove the stud. Doing it on a mill will be precise and a clean even cut with a rounded lead into the passage.
When we first had this done on our engine years ago. I was listening to Dave on the phone with ARP , Indy and T&D. After many different suggestions this is what Dave came up with.
Since then My son has done many studs for small blocks. Never had and issue for several years.