Jeff,
More thoughts. The cutterhead and ram gear box both use the same oil, so should not make a difference if they mingle. From your photo, I notice that the thrust washer and beveled drive gear are not shown. You do have the beveled thrust washer that fits between the bearing and the drive gear? the bevel side, (smaller dimension) faces out, to mate the smaller diameter of the drive gear. On my machine, it was installed backwards, was damaged, and was subsequently lost by a friend that was supposed to make a new one for me. Fortunately, I had made a measured sketch, so a different friend was able to recreate one for me.
Ron