'Legion' - The tip and claw on your extractor look fine to me.

Your "Go" gauge has very sharp corners and I suspect it does not fully enter into the "flange" that encircles the Bolt-Face.
It is probably hanging-up on the corners, where the 'Bolt-Flange' meets the Face. This would give a bogus 'fit', instead of going all the way to the bolt-face and allowing the bolt to close.

You can test this by trying the gauge against the bare bolt for correct contact. It is odd that only one gauge is beveled.

There seem to be brass particles and shavings present in your action, locking-lug recess, and extractor-notch.
Some cotton Q-tips with solvent will clean out this debris.

The Brass particles may be causing you difficulty.

(The brass is being shaved off of cartridge rims.  This can happen as they pass across the 'open' groove, that should house the shaft of the magazine cut-off lever).

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