Understanding complex planning challenges requires deep listening and meaningful, ethical engagement with people with lived expertise. This is particularly true when designing a service or system that people rely on to meet their daily needs. In this case study, a multi-faceted approach to customer engagement brings richness to understanding individual experience on specialized transit. Hamilton Street Railway used both a survey of active customers and customer journey mapping to identify ‘pain points’, highlight root causes, explore suggestions for improvement, and support future integrated service planning.