I was on my college debate team; the Nationals final round in 2003 was about this hypothetical ("Give a homeless person a dollar?") I was pleasantly surprised to recently find that it was taped and available online: http://www.parlidebate.com/recordings.php?id=36
I can't fairly condense the salient points, so I'll just encourage you to watch the video - it's long, but well worth it. I can honestly say it changed how I evaluate these sorts of situations (aside from being a very fine round of debate, but that's more of an acquired taste).
(Just to be clear: I was not one of the debaters, just happened to be lucky enough to be in the audience).
In the direction of giving - either money, or if time allows, something like what Stallman is doing/advocating. The main thing that shifted my views was the notion that even if the money is "wasted" (or might be more effective dollar-for-dollar elsewhere), there's a lot to be said for the human connection - and that even if the recipient is operating under false pretenses (which does happen sometimes), that human connection is worth it.
> In the direction of giving - either money, or if time allows, something like what Stallman is doing/advocating. The main thing that shifted my views was the notion that even if the money is "wasted" (or might be more effective dollar-for-dollar elsewhere), there's a lot to be said for the human connection - and that even if the recipient is operating under false pretenses (which does happen sometimes), that human connection is worth it.
Pardon me if this was mentioned in the debate — unfortunately I'm not in a position to watch the video at the moment — but the worst case in giving money to beggars is not just that the money is "wasted".
In the UK, the overwhelming majority of beggars are not homeless, and are simply begging to fund a drug addiction (usually to 'Class A' drugs such as heroin). A survey by Westminster Council found 86 percent of people begging spend the money they receive on drugs and alcohol, and seven out of ten of those arrested for begging (begging in public is illegal in the UK, although enforcement of the law is sporadic) had Class A drugs in their system (see: http://www.thamesreach.org.uk/news-and-views/campaigns/givin...)
In other words, when you give money to a beggar in the UK, you are more than likely funding a Class A drug addiction. An addiction that drastically reduces that person's life expectancy, and increases their chances of premature death due to an overdose.
I definitely fall on the side of the fence that actually-effective charity is superior than any "human connection" or other warm-fuzzy feeling I personally might get, though I do enjoy my warm-fuzzies every so often. I started treating them separately at some point (most likely influenced by http://lesswrong.com/lw/6z/purchase_fuzzies_and_utilons_sepa... ) and that seemed pretty helpful in a couple ways.
One trick I'm trying this year is that whenever I'm asked for cash or see a bum asking for cash and don't give any (typically because I don't want to or because I want to give less than $20 and I only have a card (and I don't want to give any time)), the next time I'm at a computer I increment a total on my home system by some small delta. It represents the total I intend to donate all at once near the end of the year to where I think has the most expected utility.
I can't fairly condense the salient points, so I'll just encourage you to watch the video - it's long, but well worth it. I can honestly say it changed how I evaluate these sorts of situations (aside from being a very fine round of debate, but that's more of an acquired taste).
(Just to be clear: I was not one of the debaters, just happened to be lucky enough to be in the audience).