325 wsm issues

First REMOVE THE FIRING PIN ON YOUR BOLT because you'll need to cycle live rounds. Using an accurate micrometer measure the brass on an unfired round at the top of the neck. Then do the same to one of your already-determined-unchamberables. Compare.

Do you use stainless steel pins and tumble to renew your cases? If so you may be "collaring" or "donuting" your brass case mouths. Be sure to chamfer inside and outside thoroughly.
 
Before you seat a bullet put a sized case in the Shell holder. Run it to the top and leave it. Then screw the seater out a ways so it will not touch a bullet If you had one in the case. Now screw the die down on to the sized case till it stops. Then you back it off a half turn and set the lock ring.

Now when you seat a bullet you won't hit the top of the on the die.

This is correct and RCBS says to back it off a full turn but in both cases, you are not crushing the shoulder. Even with being at AOL =2.850", some bullets may be reaching the lands at less than max AOL. Let us know how it goes.
 
Did you chamfer the case neck inside and out ? I skipped the inside step once with new brass and seated some flat base bullets that caused the case neck to bulge just enough to keep me from cycling them in the chamber.
I couldn't see it with my eyes but I could feel it with my fingers and of course I checked it with calipers as well and found the problem.
 
This thought hit me in the middle of the night: you said you tried unloaded brass and it fit fine. It could be a possibility that the primer is not seated deep enough. It would cause difficulty in the closing bolt.

You could use a sharpie as a poor man's layout fluid and cover brass and bullet. Try to chamber the round then check for any rubbed off areas to determine where cartridge is not fitting.
 
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