I got the same feeling. It's because he doesn't treat the guy like a person; he never calls the homeless man by his name, Keith, but keeps referring to him as a bum.
Giving this man more money, but without coupling that with professional assistance, may do him a lot more harm than good.
There's a reason why real academic studies have to pass through an ethics review, and I take issue with how cavalier this guy is about his study.
If the author of the blog has experience working with the homeless, then ignore all I've said above. But otherwise, he's operating way outside his field of expertise involving people and situations he doesn't understand, and complexities he does not seem to be aware of. This is dangerous.
Is it really so preposterous to assume that this guy's medical expenses caused his financial difficulties instead of assuming that he wasted everything he had on drugs? Sounds believable to me.
It'd be quite difficult to answer this question in a scientific manner, but I bet that large investments kill more businesses than they help (vs. bootstrapping)
And you can't seem to make your point without name-calling. Kudos.
This is where even a cursory familiarity with the issues surrounding homelessness in your area would be greatly helpful. A huge portion of the homeless population has severe substance abuse problems and/or mental health issues. I highly doubt a bum is going to be spending his panhandling dollars on hookers, but alcohol and blow is more than likely. Given what I know of the proportions through volunteer work, it is entirely unsafe to by default assume a homeless person does not have significant substance abuse problems. Sadly, this is one part of the homeless stereotype that is rooted in reality.
This isn't to pass judgment, but rather to point out that if you really want to help people get off the streets for good, and bootstrap themselves out of poverty, you need to do a lot more than just give money. For a great many homeless people the cause of their homelessness is a lot more than just being down on their luck, it has to do with long-standing problems - substance abuse, toxic environment, and other negative influences. Giving money without resolving these other external issues will just exacerbate the problem.
And note that we're not talking about poor people, we're talking about the homeless. These are people who can't show up to an interview showered with a clean t-shirt - they are not at all like the "merely" poor. Do these guys make enough from panhandling to afford even a shitty room somewhere? Odds are, no, and that's pretty much a bare minimum requirement if your goal is to get off the streets, clean up, and get employed. I contribute to organizations that do this for this very reason - my money is doing much more good (heck, it's at least not doing bad) in the hands of professionals who are able to offer an environment where people have access to the help they need, and the stability to make lasting changes in their life.
And FYI, I'm contributing significant amounts of my money and time to this particular issue, a lot more than change most people give to the homeless in any given year. What are you doing about it?
in general, saying "it's not [some extreme caricature of a position]" isn't much use in arguing against anything, and doesn't really help anyone much...