The purpose of this study was to develop the measurement model of rationales for homelessness which combines individual and structural accounts with respect to how individuals become homeless. The study, further, developed structural model overarching from adverse childhood experiences to pathways to chronic homelessness. In addition, the multilevel model was created and tested in order to test the impact of two aggregated variables of rent rate and unemployment rate in macro-level on the measurement model of rationales for homelessness in micro-level. The measurement model and the structural model fitted well to the data, and configural invariance was found across gender, ethnicity, and the type of homelessness. Gender differences were found in pathways both to become homeless, and to become chronic homeless. The findings from three model tests clearly presented that the combination of individual and structural accounts explained both rationales for homelessness and pathways to homelessness.