Yes, judgement always plays a huge part.

How about this for a theory? Perhaps the stall speed of an aircraft should have a bearing on whether or not one should pull the chute? The logic being that if your aircraft wing stalls at a speed that would be fatal in a collision with ground obstacles, then unless you can be sure of avoiding said obstacles, you should pull the chute? (assuming you have one)?

You don't see many fighter jets landed dead stick. A fellow tried it a year or two ago near Mirimar NAS, with fatal results not only to himself but also people on the ground. Very sad.

But again, high stall speed? Pull chute (or eject over unpopulated area). Slow stall speed in acceptable visibility and terrain? Go for it.