T-Star: I have been reloading for over 25 years and yes, I know the difference between a crimp and a cannelure (by the way, both bullets and cases may be cannelured). The problem with W-W 9mm Luger brass is a taper crimp won't hold the bullet securely, thus a cannelure on the case (at the base of the bullet) is required to prevent 'telescoping'. The results of the American Rifleman article years ago mirror my experiences, thus ALL Winchester 9mm Luger brass goes into the recycle bin.
Winchest brass is about all I use. I have yet to have a problem with any of it in 9MM. Some plated 9MM brass I have used is less than .355 in diameter which contributes to what you are experiencing. I size all my cast 9MM boolits .357 and don't they work fine with a taper crimp. I crimp with a Dillon crimping die. I don't belioeve your opinion of Wincherster brass is founded on fact. I would also question the authority of some writer in American Rifleman written "years ago" as being relevant all these years later. If I were you I would seek out a different sizing die to see if that isn't your problem.
Take Care
Bob