Tough Love?

As an utterly inappropriate follow-up to yesterday's post, here's a question from C. Ewing:

This is a question that has come up at work periodically. We work with people who (typically) can't help themselves, but when doing any sort of volunteer or charity work there is always the risk of dependency, and the risk of people who are simply trying to abuse the system. The ideal scenario is that we simply get them where they need to be as best we can (the essentials for living), and let them take it from there. But I've had several clients come back to me later on, wanting other help. Now, when it's available I make the effort to give them that help, but I sometimes wonder: am I becoming a handy tool for them to utilize, and in being that tool am I preventing them from developing their own means and independence? Am I hurting more than helping? When is tough love needed/demanded? Is it sometimes best to let people "tough it out", and if so, when? How do you know? Now, sometimes it's obvious that the person doesn't have the financial means for certain things. But there are gray areas where it's not clear they couldn't manage it with effort. How do you know when to let them "sink or swim"?