I'm thinking it might be worthwhile to engineer a scalable, high-traffic city(maybe city's the wrong word, it could be sprawling and fast, instead of dense and slow) from the ground up, somewhere there isn't one already. You don't need to build the transit immediately, you just need to have the restraint to reserve the space for a time when you will want it. Other useful constraints aside from transit reservations, might include: setting aesthetic standards (line of sight corridors[through zoned height restrictions] to natural beauty, stylistic restrictions, above-ground pedestrian accommodation planning), extensive mixed-use zoning in the sprawl, multiple downtowns (hierarchy of pedestrian/two-lane/light rail accessibility > main street/express light rail > freeway/full sized rail arranged in superblocks).

Added: Three-dimensional land parcels would solve a lot of the problems with properly valuing natural beauty, direct sunlight, and underground access.

Added: Environmental (noise[aggregate peak SPL, loudness], ground vibration[aggregate peak amplitude], air pollution[aggregate peak particulates, ozone, maybe fuel fumes, maybe heat], ground pollution, EMR [including radio and light]) sensor networks could be used to make it simpler to uphold agreements and ordinances, or litigate environmental property devaluation or damage (reduction in air quality, disturbance of quiet, excessive night time light, ground shaking). You could also include on-board detectors for things like gunshots, car crashes, or desperate cries for help, to aide emergency services. Data like these could be made completely public so that public offices don't need to waste their time determining access.