Terrance Heath wouldn’t think of driving to work. His law office in San Francisco overlooks Union Square, a shopping mecca where the daily snarl of honking taxis, open-top sightseeing buses, and double-parked delivery trucks make curbside parking nearly impossible. Parking in the garage under the square would cost more than $30 a day—too much for Heath, a single father of two.

That was before the launch of SFpark—one of the most far-reaching innovations in US parking policy since the...

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