With the fired brass giving you issues, it sounds like the same sort of issue that happens with the 6.5 PRC. There are several articles on the subject. IMO Alex Wheeler did a good job of explaining this problem. In a nutshell the chamber is too tight near the case base and the dies cannot size fired brass enough for easy extraction. Some cases are stoutly built and once the base diameter increases and won't be sized back for easy extraction. It can be the die you are using, or the chamber is just too tight in the base area.
The solution is to use a reamer that is a bit larger in the base area or sand that portion on an existing barrel. I have seen this sort of thing with the RUM, WSM, and RCM cases.
Before this was common knowledge, I made a small base die by cutting down an extra RCBS FL die removing the top and bottom with a carbide tool bit on a lathe. It helped with a sticky RUM that my friend and I have, but wasn't perfect.
After the clicker discussions, I took the two 338 RCM barrels off my rifles and chucked them up in the lathe and sanded the base portion. This fixed the issue.
You can view two videos on this subject. Die fit and clickers found here:
www.wheeleraccuracy.com
Hope you get it figured out.