Greets,
From your pictures, I would say that the shifting dogs on the gear are worn and could cause problems. It would be prudent to also check the engagement holes on the mating gear for wear as well. Ideally, the shifting dogs and mating holes should have clean, well defined edges. You might also want to check the shifting forks for excessive wear on the fork ends. Also, check to be certain that none of the shifter forks are bent and that the shifter drum and slots are not worn. Careful examination of the tranny parts at this time would be to your advantage. Happy wrenching...