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Drilling the larger hole may not be as pleasing to the eye as a smaller one but, no wires have been cut (inviting in corrosion) and nobody will notice. I tried to saw a small piece of wood on the console (in place) a few summer's ago with my new engine set up. I know I'm "skilled enough" to handle this, and there's room to get the saw in there. It was like a magnet, two saw strokes with the jig saw binded up the blade, and threw the saw over onto the new ignition wire harness before I could shut down, "choppity chop" , I had to splice and seal all the wires back on a new harness, new curse word's were invented that day.
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Ric, sorry to hear that you had to cut/file the hole and could not get the pins out. Sometimes you have no option. Well, good news is, no cutting and splicing, so that's a plus.
Just in case you think a larger boat would give you more room I'll share a bit of my Montauk rewiring. There is all kinds of room in the Montauk console, for a skinny twelve year old, which I am not. After two weeks of climbing half in and out of the side access door to the console I had blood; and black and blue on the backs of my arms and on my back for weeks.
I know this didn't help you one bit but know many of us were feeling your pain as you lay under the dash.