Here are some comments inspired by John the Methodist and commentators at his site:
It’s been said, “Give a man a fish; you have fed him for today. Teach a man to fish; and you have fed him for a lifetime.”
This helps illustrate problem of timing when it comes to measurement. When you invest yourself in teaching a person to fish you will – at one point in the process, appear to be cruel and heartless. “Here is this poor man, needy and starving, and instead of giving him a fish, you make him wait until he can learn to catch one himself.”
Or we could change the image a little. “Here is this poor person without a job, and instead of giving her a job right now you make her go to school first. How can you be so heartless?”
With current techniques of communication and travel, we can know more than ever about the tremendous needs of people around the world – and we have the means to send them resources. We know how to sell all we have and give all to the poor. But is that a “give a man a fish” or a “teach a man to fish” solution? Something that will help in the short term but be disastrous in the long term (unless having large numbers of people who have given away everything and now need other people to care for them is not seen as a negative).
Admittedly, the this whole idea of fishing is unbiblical (though other ideas of fishing are present in scripture, this quote comes from elsewhere).
So what can we do given the problem of time? Here are a few ideas:
1. Live as grateful recipients of God’s grace. Nothing we have is ours merely because we deserve it.
2. Live as stewards. God has put resources under our control to use for his agenda. In the parable of the talents praise came not for immediately giving the talents away, but for multiplying them until the master called for them.
3. At any given time be living in such a way that a picture of your life up to that point would show you to be generous with the people around you.
4. Redefine your sense of personal gain and prosperity to include the actual well-being of the people around you.
5. Give more than you loan. If someone pays you back, that’s ok.
6. Trust God to take care of your finances and possessions more than you trust yourself (or the government) to do so.
Bandits No More 
My former pastor Tom Thomson once pointed out that if the church in Jerusalem had not sold off all their means of making money, they would not have been in the position of having to receive donations from the churches in other cities. That point dovetails with yours about having former givers turn into the needy because they didn’t use the principle you illustrated.
Your examples above set forth a false dichotomy. There is nothing inconsistent to giving a man a few fish while (and to support him while) he learns to fish. It is indeed “cruel and heartless” to allow a man to starve because it takes a long time to learn to fish. My parents certainly “gave me a fish” (a lot of them) while I “learned to fish” (went to school, got a college degree). There is no either/or here.
Your example of “Here is this poor person without a job, and instead of giving her a job right now you make her go to school first. How can you be so heartless?” is a perfect example of the false dichtomy. When I went to school, and both my kids went to school, we all had part time jobs to help pay for the school. We were “given a job now” AND “went to school”. There is nothing inconsistent about “giving her a job now” at the same time you “make her go to school” My daughter, for example, had a job in college where going to school and passing her courses was a requirement for getting and keeping the job. Where was the inconsistency there?
Yes, what you suggest IS heartless, but the heartlessness is yours because of the false dichotomy you have artificially set up, based on the false allegation that a choice must be made between “giving a fish” and “teaching to fish”; between “giving her a job” and “making (allowing) her to go to school”.
There are of course those in our midst who my never be able to “learn to fish” sufficiently wellto never require the gifts of fish from others, just as there are many who (once they are adults) may never require the gift of an occasional fish. But, in your example above, if it is reasonable to “require her to go to school”, it is equally reasonable to give her a job now to allow her to do exactly that.
Giving of our fish to others while we teach he others to fish is how we “multiply our talents” and how we “include the actual well-being of the people around” us. If her well-being includes going to school, how could it not include having access to the means to allow her to go to school?
Rick, I think you miss my point. I wasn’t arguing for either the first (give a fish) or the second (teach to fish) option, and therefore was not setting this up as a dichotomy. I was trying to show that while we go about doing both kinds of activities, we might, at any given moment (the moment of judgment or evaluation) appear to only be doing the one, when someone might say the other is called for.
In my number points, #3 leans in the direction of giving fish, #2 in the direction of teaching to fish.