Aging building technology creates hidden operational costs, tenant friction, and escalating risk — but wholesale rip-and-replace is rarely feasible. In this interview episode Alex Morgan and guest Michael Harrington walk through a pragmatic playbook for identifying technical debt in commercial properties, prioritizing retrofit work, and delivering phased upgrades that preserve uptime and tenant experience. We break down common debt sources (legacy protocols, unsupported firmware, proprietary chokepoints), three practical retrofit approaches (temporary bridges, strangler/segmented replacement, and prioritized rip-and-replace), and the coordination, testing, and financial framing that make projects fundable and operable. Listeners get concrete examples from Michael’s portfolio experience, decision checkpoints to avoid costly mid-project surprises, and communication tactics that keep tenants and vendors aligned. This episode is for owners, facilities leaders, IT teams, and GCs facing the realities of modernizing systems in occupied buildings.