I have had my 911 since last September, and although I topped-up the trans oil earlier, I just now got around to changing it. The magnetic drain plug had this nice surprise stuck to it; broken dog teeth. No wonder shifting into second is inconsistent - I take it very slow and mostly have no trouble.
The old oil was jet black and there was a lot of glop that came out with it. My guess is this: Since five of the teeth show very little wear (except for being broken off), but the sixth shows a great deal of wear in addition to being broken, could it be that the unworn teeth were broken a long time ago (the oil maybe never was changed) and the worn one was broken recently? All the teeth are magnetized, by the way.
How serious is this? I can't shift quickly now, but I also need to change the shift coupler bushings and the engine/transmission mounts. What do I face in the short term?