I use a plug gage (small ground cylinder about 2 inches long in a set where each is 0.001 inches bigger than the next one) on a case known not to be crimped. I then use that plug gage on the case in question and it should easily insert into the primer pocket with no more than sliding friction. If not I use a chamfering tool to remove the crimp. I don't stop with the chamfering tool until the plug gage fits.
Failure to get rid of the crimp totally will result in some primers collapsing while you try to force them into the crimped primer pocket. With the shortages of primers right now and I suspect in the future, due to the hoarding going on from the Obama election and the Connecticut shooting and the impeding gun control measures that are sure to come out of the feds, the last thing you want to do is ruin primers!
As an aside I have found all the tools sold to remove the primer pocket crimps to be less than adequate. When I gage the results all the crimp is not removed and the primers go in hard. I also have the swage tool sold by Dillion. It requires that the thickness of the cartridge heads be constant. I have found that on Mil Surp once fired brass, even with the same head stamp, that not to be the case and all of the crimp is not removed (Dillion instruction warn of this problem!).
LDBennett