... dude works for 20 years at minimum wage, and then when he gets sick with a non-acute ailment expects everyone to drop their shit and make his life better as a free ride -- and that's an example of "good planning done in by external forces"?

That summary is incorrect. He worked for 20 years at his chosen profession, lost his job, then found work at minimum wage instead of no work at all, then got sick.

Could he have saved more during those 20 years, and therefore done better? Undoubtedly. What size should an emergency fund be? Let's ask Google:

Though personal finance experts agree emergency funds are necessary, there’s no consensus on how much is enough. Some say you need save a year’s salary. Others believe $1000 is sufficient. Most advice tends to fall someplace in the middle.

says GetRichSlowly

Bankrate recommends creating a special account that you don't touch, except to pad it with 3-6 months' worth of expenses.

says LifeHacker

Most experts agree that you should keep between three and six months worth of your living expenses set aside in your emergency fund.

says About.com Financial Planning

Financial experts recommend that people maintain a cash reserve large enough to cover three to six months' worth of household expenses.

says Investopedia

Enough money to deal with major medical expenses following a prolonged period of un- and underemployment.

says... um... nowhere, as far as I can tell.

Only archived in wetware, I'm afraid.

This seems to leave you more vulnerable to many biases.

... dude works for 20 years at minimum wage, and then when he gets sick with a non-acute ailment expects everyone to drop their shit and make his life better as a free ride -- and that's an example of "good planning done in by external forces"?

He worked in some ambiguous field for 20 years until he lost his job in the economic collapse, then he started working minimum wage, and with the insurance available to him on that job he was unable to afford treatment for cancer. Cancer is among the more acute ailments one might reasonably expect ever to face; if a tumor is malignant, that is, cancerous, then if untreated, it is unusual for it to be nonfatal.

If you start completely mischaracterizing data that is held up as a counterexample to your position, it's a good sign that you're being controlled by your preconceptions.

As Desrtopa and dlthomas pointed out below, your summary of this guy's situation is incorrect; I think that your wetware-based data collection policy may have something to do with this.

Speaking more generally, I am not sure I understand your "big picture" view. You say:

...and then when he gets sick with a non-acute ailment expects everyone to drop their shit and make his life better as a free ride...

Does this mean that you're against the very idea of having a social safety net ? Or are you merely saying that, while a safety net is a good idea, this particular person's expectations are unreasonable ?