Teaching -- How far do you hold their hands?

This is a tough question for me. I am care-taker kind of person; a sucker for a hard-luck story. But eventually, even a manipulative student who plays the sob-story card can push me too far. I do eventually come to the conclusion that I am not doing them any favors to keep reminding them about assignments, keep explaining things again. I also begin to feel that it simply is not fair to the other students who paid attention in the first place. They read the syllabus. They read the assignment. They did the work and got it done on time.

How fair is it for me to remind the wah-wah student more than twice? To explain things separately from what I give the rest of the class? Sometimes, it helps me put things into perspective to listen to my daughter vent at home. She is a high school student, but she works really hard, and gets really ticked off at the students who expect a free ride. Especially when they manage to get one.

So the tough question is always, how much is legitimate confusion and need for clarification on the student's part? And how much is looking for a free ride? They just haven't bothered to pay attention in class or read the syllabus. Or perhaps, they are learning disabled and I don't know it. Tough call!