In this narrative review, we provide a historical overview of the rising trend towards vehicle-based living, focusing on mature-aged, hypermobile, gig workers. We draw on findings from several bodies of literature, including road-based tourism and digital nomadism, as well as narratives from popular culture artefacts. Focusing on the nexus of tourism, housing, senior entrepreneurship, remote work, and active ageing, we identify opportunities for the growing silver economy, including ways for regional areas to attract patronage and leverage purchasing decisions associated with shifting population demographics. Scholarly awareness of this previously neglected, and largely invisible cohort of society is weak. Further research is proposed to aid in better understanding the needs of mature-aged, hypermobile gig workers, and associated market opportunities.