Hm, this encouraged me to run some more playthroughs, and I want to take back some of my praise.
I had initially gone for a longish commute to save money, but now that I look harder at living close (and find out that the car is mandatory regardless), the savings are bizarrely low. Presumably the character lives in a smallish town since parking a car isn't expensive, but living distant to work isn't a major savings?
Other options I hadn't picked initially were shockingly bad: applying for a scholarship for the student gifted program got me a job strike, because the player (unlike the character) doesn't get to find out that it'll require an unapproved absence from work until after the fact!
And then I tried to look up some stats on the 2011 ACA rules. You're right: even at $18,000 (40 hr/week, 52 weeks/year pre-tax at the warehouse job) I can't reconcile the options listed. In Medicaid-expansion states the plans should be vastly cheaper, and even in those that declined it the mandatory coverage fee should be absent or waived. For that matter, the lack of an offer to buy paired health insurance (mandatory to offer under the ACA) is a pretty manipulative thing to pair with a major dental bill.
It looks like I got substantially lucky with my initial choices. I understand that the game is trying to show a typical case, not an ideal one, and that being poor can mean a lot of unexpected expenses and setbacks. But things like "oh, surprise, that option actually meant taking off work without permission!" don't represent the difficulties of poverty, they represent the difficulties of a game made to punish sensible-looking choices.