Also, the fact that the fit was "less tight" as I screwed the sizing die in farther...does that not mean it is a tight headspace issue?
That was my thoughts exactly! Personally I would set my shell holder on a piece of flat sand paper and hone 2 thou off the face of it being careful to measure with a set of calipers as I go to ensure squareness. I've done it before, its pretty easy. If the brass has been fired more than 3 times you could also anneal your brass and likely solve the problem since the shoulder would not spring back so much
Trystan