The only time I ever had "hard case extraction problems" was with overpressure loads.
The worst-case scenario would be that he has a ringed chamber and that his loads are hot enough to leave brass protruding into the ring, which happens only half the time due to external environmental temperatures. To check for that, look for a shiny ring on cases where they were scuffed during extraction.
2nd - I've twice run into manual starting loads that were already at maximum for the rifle I was using it in. One was a .25-06 load from a Nosler manual. Always start with the starting load, which should be 10% below the maximum stated pressure. He stated his loads are .5 grain below max listed but he is probably overpressure for his rifle.
3rd - The cases were not overloaded or above max loads, but the OAL for a particular bullet profile set the bullet into the lands and caused the overpressure. In general, if you are loading a bullet in contact with the lands, the pressure will be about 20% higher than when the bullet is 0.020" to 0.050" back of the lands (depending on the shape of the ogive).
This can be avoided by using a Case length gauge and finding the Max OAL for a particular bullet in the rifle concerned instead of just taking some book reference.
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