Okay, I guess it is possible to get the up/down encounter with the pins pulled out. As long as you've won enough fights, I guess? I've now gone down for the second time, and got the 'barely seems to move' result, with the pins pulled out.
Also, I'm not sure what controls the messages you get when climbing down, but I think they determine the type of XP you get on the next level. "The maze in your hands moves in intricate patterns." seems to have lead to Perception XP, while "The maze in your hands barely seems to move unless you haul at it." seems like it resulted in Strength.
Edit: I've now hit a masked spider twice in a row. I fought one, pulled the pins out, then ran into another rather than getting the XP encounters. So I'm not certain how this is working.