grey,
First, your lensboard is drilled to be used with a flange. The flange has threads in it and is mounted to the lensboard with screws (hence the holes and Issue #1). To mount a lens to a flange, you simply remove the rear element and screw it into the threads inside the flange.
It looks to me as if the hole for the flange is actually to big. That's what is keeping your locking ring from hitting anything
You may be able to reverse the lock ring with the collar toward the lensboard and get purchase that way. If not, you may need to buy a new lensboard with a proper-size hole or, alternatively, you could get the correct flange.
Best,
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