Abstract: The present invention is a system and method for delivering optimized road maintenance analysis to a municipality. The instant innovation scans roadways for distressed street surfaces, damaged signage, and other less-than-optimal municipal assets. Data is collected by multiple municipal fleet vehicles as such vehicles drive upon roads within a municipality. Collected data are analyzed by a machine learning algorithm using criteria that most directly correspond to multi-year road quality predictions. The instant innovation provides to a user one or more suggestions and scenario results for roadway maintenance strategies based upon the data analysis.