Lack of parking isn't a "problem"--what's the city's breaking point?

It's funny how we hear so many neighborhood residents and even Alderman (including Nataras) say that lack of parking is a 'problem'. That's news to me. Was it a problem when the loop was built a century ago? Was it a problem when Chicago's neighborhoods were built? Just when exactly did this become a problem? What exactly do people expect the solution to be? Should Chicago dissolve itself and no longer be an urban city? But to get to the point of this thread, at what threshold of traffic congestion in Chicago (due to on-site parking and garages being built all over the place) does the pressure (for the masses of people of decent means) to use transit outweigh the ignorance, laziness, or even embarrassment of its use? What's the breaking point, if there is one? Of course, I'm referring to its day-to-day use for everything, not the morning commute to work downtown. At what point will Joe the attorney in Lincoln Park decide to take a bus to Armitage instead of driving? Will Chicagoans ever be pushed to this threshold? I say this because I sincerely believe that people will never choose transit over driving unless driving becomes far, far too inconvenient.>