> These things only work for some of the residents (predominately younger residents without families).

Leaving aside the fact that seeing families on buses is not remotely uncommon, the same statement could be said of automobile modes. Those who can't legally drive (which probably constitutes a quarter of the US population) along with those too poor to afford automobiles are at least partially excluded from the benefits of automobile infrastructure. Given current technology, a transportation system for everyone needs to facilitate the use of a variety of modes, even if no particular mode serves everyone.

> And those parts of Chicago suffer economically for it.

Do you have any data for that? Most of the literature suggests that the provision of free parking reduces economic prosperity. The simple theoretical explanation is that parking should be provided at cost, just like most goods and services. But there is also empirical evidence to back this up. For instance when Old Pasadena raised street parking rates in the early nineties to deal with a dearth of parking in their commercial district: "The cities sales tax revenue tripled within the first year."* That's one anecdote, but consider googling Donald Shoup for more literature and data.

There are two additional theoretical benefits to using pricing to adequately supply parking. First, it favors persons who value their time relatively more than their money, which are exactly the kind of people who tend to buy stuff in stores. And two, increased parking rates can increase turnover, which in turn increases total sales. For more info on the importance of turnover, check out this SNL sketch: http://www.nbc.com/saturday-night-live/video/the-olympia-res...

*Speck, J. (2012). Walkable city: How downtown can save America, one step at a time. New York: Farrar, Straus and Giroux. (see page 134 for the quote on Google books).

Making street spaces free would actually make the problem worse: the price is already well below what I'm willing to pay, the problem is that I'm unlikely to find a street space at any price (below the cost of a ticket) near a given destination.

To provide free parking in popular destinations such that it never completely fills up, the city would have to buy property (shutting down or relocating the businesses already on it) and build parking structures on it.

Families across New York City give birth to children, get them to school, do groceries on the back of its transit system.

As do people in Hong Kong and Tokyo and Singapore and Seoul and London and Berlin.

Come and visit Copenhagen. You can see people from 6 to 90 years old riding bicycles, and younger children being carried in box bikes etc.