This is a great question, and let's start with the overarching situation before I give my opinion on this.
As a country, the United States has decided that it will provide a scanty minimum level of assistance to those in need. This is a pittance, far below the earning power of someone working at minimum wage but is a frank realization that people aren't going to starve silently.
Giving people bread is cheaper than facing hungry people willing to commit violence for it; and [nearly] anyone who has gone four days without food is going to be desperate for it. This reasoning applies to drinkable water, medical care or basic safety needs. This is why we have a social safety net, and while people with no skills and no ability need to eat something.
This whole system largely emerged in the Great Depression, when the previous model of charitable giving became woefully inadequate to helping desperate people. Its existence may be one the few things that kept the Great Recession from mass social outcry.
Chris and Barb are vicious, pathetic people with serious mental issues, but they have as much call for that minimum aid as anyone else. Far worse people receive government assistance; and I believe that as a democratic nation of the people for the people by the people, the Tugboat should sail.
The Tugboat is institutionalized charity; no American can refuse to pay their taxes and get away with it; nor their social security, nor even sue on how their tax monies are used. All Americans charitably support CWC via this method, and I respect that the alternative is likely worse. Because of the Tugboat, CWC won't starve. He might be uncomfortable, he might not even fulfill his basic desires, but he'll never be cornered into being so desperate that he becomes violent.
Donations are at the discretion of the provider, and I make no judgement about those who enjoy helping someone like CWC--I don't like him, and I wouldn't help him, but I can understand that others might. But I find no joy in helping people who are mean or impolite to others (and I'd given a bitter old woman a dollar--she decided to ask for 10$ immediately afterward. Never again.) Chris will not use the money well, he will not use the money to better himself or to make meaningful improvements to his life. Most Likely:
He probably would by a PS4.
He probably will buy many games for various consoles he already has.
He might buy the services of a Professional Heartsweet.
He might buy Adult Media.
Given enough money, he might even try a legal gambit against trolls of some variety.
So if helping Chris or Barb makes you happy, or if you've got so much money that alternative methods wouldn't make you happy, donate to a most unworthy fellow. But you've already paid your charity to this Lolcow through your taxes; if he wants more he'll figure out a way to get it or he'll go without. That's the reality all of us live by; its certainly fair to him as well. But this is a tonic of reality he's ignored for his entire life; his only chance at a better life is to DO SOMETHING about himself. He's the only one that can make that decision; IMO, coddling Chris teaches him nothing.
