The biggest challenges to change are comfort and convenience. Regarding transportation, another obstacle is the pervasive political obstruction with the governmental mindset to maintain its status-quo.
Possibly the largest challenge for transportation is existing land-use development. Since a specific mode of transportation dictates its land-use, replacing a type of land-use design to accommodate a mode of transportation designed for a different mode of transportation, turns the land-use into a dysfunctional design.
This is part of what makes this Ameliorate Journey worthwhile. Identifying the realistic transportation and land-use issues, and providing realistic solutions.
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The Ameliorate Journey Course goes into understandable detail; identifying functional aspects and impacts of the various transportation methodologies as the influence urban growth.