Rich suburbs do fine. Many suburbs of Boston have high income earners and high property values resulting in sane levels of property tax that actually fund those regions adequately. Most of the suburbs Strong Towns criticizes have $250k homes with household incomes between 40-50k and it’s impossible to tax those residents enough to pay for their infrastructure.

These are towns that were founded in the 1800s at the latest and some in the 1600s...

Were they bulldozed and rebuilt into car-centric development?

From my understanding Strong Towns think "lower density, less intensely urban development" towns are fine. E.g. at 0:57 of the video, it's anything but intensely urban development.

"In this example, a 100-year-old commercial block, built in the traditional style of development, drastically outperformed a shiny new development, created in the modern car-centric style."

I would describe Arlington (1635), Belmont (1849), Waltham (1884), Watertown (1630), Lincoln (1754), Wellesley (1881), Newton (1688 town, 1874 city) as being substantially car-centric with respect to the majority of adult residents of those towns/cities owning a car today and using a car or car service more than 250 days out of the year. Arlington would be feasible to get by without a car in many of its areas. Others would be much more difficult in the majority of the land.

Looking at satellite images I would predict they would not do well financially with the infrastructure costs.

But then I look at the housing prices. TimPC's explanation seems legit.

Speaking as an Arlington resident, I would not describe it as "car centric", although cars are accommodated far more than I would like. It's still a classical streetcar suburb. The majority of Arlington's housing stock is from multifamily buildings within a couple of minutes walk to high frequency bus service (~5 minute wait).