Prolonged lengths of stay (PLOS) impact patient outcomes, healthcare spending, and bed availability. Many patients stay beyond medical necessity due to complex barriers to discharge, including conservatorship applications and insurance coverage, shifting the provision of care from acute to chronic on medicine wards. We aim to understand the impact of this shift on healthcare staff workflow, interactions, and wellbeing through 23 key informant interviews analyzed using grounded theory. Our findings highlight PLOS as a contributor to burnout, with implications for patient care and staff job satisfaction that necessitate additional support for caring for this vulnerable patient population.