I don't get it (and i may be missing something obvious). If he cannot get the stem to go into the steerer, why would he need to tap/die the threads on the drawbolt for the wedge on the quill stem further? That would be a "not tight enough" problem, not a "i can't even get the thing to go into the steerer to the depth i want" problem.

I feel like I'm missing something here, and i third (fif'?) the recommendations to measure the steerer ID.