I was thinking more about Sebastian Mallaby's mocking of requiring insurers to cover wigs. It is, as Ezra suggests, precisely the kind of thing that most people wouldn't think to add to an a la carte insurance policy, precisely because most of us aren't really equipped to sensibly make such decisions. More than that it highlights the pathological lack of empathy someone like Mallaby must have.
Here's a guy who undoubtedly has pretty damn good insurance through his employer. If an illness strikes and he's unable to continue the backbreaking work of typing a couple of columns per week about how other people have too much insurance at a very minimum I'm sure his employment contract contains a long term disability rider to ensure he'll keep his insurance and a hefty percentage of his salary. Since he's one of the gang of tenured pundits it's likely they'll just let him contribute when he can and keep paying him. Given his hairline it's true he might not bother with a wig, but even when he's able to work he'll be able to phone it in from home or the hospital. If he has a family there's probably a spouse who can pick up the slack in the childraising duties. If not, well, there's no problem there then.
I'm not going to claim to have a deep understanding of living life as a member of the working poor - and, no, years of being a relatively impoverished grad student don't really qualify - but I do know the experience of someone in that situation is exactly like Mallaby's... not. To eat and feed their kids - let alone keep their insurance if they have it - they'll have to keep working as much as possible in jobs which require a bit more physical activity then flicking fingers across a keyboard, and a bit more contact with other people than a telecommute.