Several questions: Are you buying virgin brass and loading it or are you shooting the factory rounds in your .300 WM first?

Your gun: is it a factory made gun or custom chambered by a smith?

Are you full length resizing?

Whose dies are you using?

The .300 Win Mag headspaces on the belt like most belted cartridges.....these cases can also contact the chamber first on the shoulder just behind the neck and bullet. I had this happen with a .257 Weatherby....I thought my die was bad and I returned it to RCBS and they checked it and said it was good.

Have you taken a full length sized (empty) case that normally wouldnt fit the chamber and cut the case in half totally eliminating the foreward shoulder and neck to see if it does chamber under that condition?...If it does then there' s reason to believe your chamber is short.