Greetings again @BenTheBuilder,
Although frustrating at the time the difficulties you are having will teach you much.
So to summarise:
1, Factory ammo chambers.
2, Some of your once fired brass from your rifle that you have sized chambers and some does not.
3, The reason seems to be the length to datum being longer on the cases that will not chamber.
So we know that the dies that you have can produce cases that chamber but for some reason do not always.
My suspicion in now on your lube. Micky eloquently stated some reasons to ditch the Lee lube and my experience with it echoes his so if you have not already done so replace it with something better. The 7mm WSM has little body taper and a steep shoulder, both of which require a top lube. I am using the Hornady one shot which some like to bag and the Imperial Sizing Wax seems to be top of the heap but is more expensive. You smooth this on with your fingers to the body and neck, but not the shoulder. The reason in not lubing the shoulder is to prevent lube dents which I think you have experienced. You may have to clean out the interior of your die to stop them. When you are sizing if it gets tight back the case out slightly and then complete the sizing. Take the case out wipe it of and re lube if needed. You should feel the shell holder come to a hard stop when it comes into contact with the die.
To help things along see if you can find an experienced handloader to mentor you through this stage. One thing I suggest that you NOT do is to alter the die or shell holder in any way. They are fine, It is the other ducks that we need to get in a row.
Regards Grandpamac.
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