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I set up my seating dies using a factory or previously loaded round ....place round in press,lift to top of stroke and slowly screw stem in until the handle gives a wee twitch...the die body itself does bugger all in the seating process unless you have it screwed down far enough to crimp AFTER the projectile is right down...so try it with die body up higher,maybe two full turns?? from where it is now,then set stem as above and try it.
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as Cam has said...champher case mouth well...stuffed if can see any in photo...dipping necks in powdered graphite helps no end in making thing slide in smoothly too,I do mine before resizing and it seems to make life much easier. boat tail projectiles are always easier to seat than flat base,but wit ha good champher/countersunk neck even flat base slip in easy.....also rotate your round half way through seating projectile..IT DOES help to improve concentricity/straightness if final product.
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Im pretty sure the cases were sized without lubing inside the neck.