Dartin for Divorce

The problem is having it 1 side in the hole shows the threads and the other side still is smooth and flush due to old screw still being in there. I just dont want to go up another drill bit size and risk blowing the entire hole out and having to go to a larger bolt size.

That's definitely a challenge. Have you got a couple picks to try and spin out the remnant? A tap may just catch and drive the left over bit further into the hole.. Don't want to damage those windings.