Not to burst your bubble, but his health plan is pretty good. I have a very similar one. It's shocked me too that you can get a good plan if you are willing to take a very high deductible..
And ironically if I took my deductible each year I didn't need it and burned it (or gave it to charity) I'd almost break even on my low-deductible 'old plan'. When I left employment the Cobra for my plan (2 people) was 980/month. I now have a HSA-style plan that's $170/mo. It has a ~5K-per-person deductible (x2 for two people). 100% coverage after the deductible is met. I'd about break even each year if we both simultaneously came down with cancer. But since we're healthy I get to pocket the 10K or so I save each year.
Most cities you can get by without a car. I prefer it, actually, it is a lot less stress than driving and a lot healthier. But, yeah, if you are like the folks who got a 'great deal' on a house in Stockton in 2007 and are now commuting from there to Santa Clara, I guess bikes are out of the question. It's all about live-near-where-you-work (or vice versa).
The author states he's got a $100K in savings - That's a lot more safety net than your average American. Do you have that kind of safety net?