Understanding underlying mechanisms and pathways that lead to chronic homelessness would help develop intervention strategies that could help prevent subsequent episodes of homelessness. Quantitative data for this cross-sectional study was gathered by interviewing individuals who were homeless in the State of Arkansas, using a structured survey between 2007 and 2011. Qualitative data was gathered using semi-structured interviews between 2016 and 2018. Chi-square statistics and a multivariate logistic regression model was used to analyze the quantitative data, while phenomenological methods were used to analyze the qualitative data. Nearly half of the study participants identified themselves as being chronically homeless. Chronically homeless adults in this region were significantly more likely to be older men with no family ties, more likely to be victims of domestic violence, have higher rates of physical health problems, and have alcohol and substance abuse problems. Results from the multivariate nominal regression revealed that individuals who reported themselves as chronically homeless were more likely to be in the 50 years or older age group. In addition, study findings highlighted a dynamic interplay between three biopsychosocial risk factors for homelessness. Fostering development of inclusive sustainable communities, intergenerational relationships, and shared housing practices could help ease such social inequities and prevent problems such as chronic homelessness in older homeless adults.