For 5 properties, the analysis depends on your equity position and risk profile:
Worth it if: You have significant equity ($200K+ per property), properties are in different states, you have high-risk tenants or property types (commercial, multi-family), or you're planning to scale to 10+ properties.
May be overkill if: Properties are all in one state with moderate equity, you have good umbrella insurance ($2-5M policy), and you're not scaling rapidly.
The typical structure: Wyoming or Delaware holding LLC → individual LLCs for each property. Benefits: each property's liability is isolated, and the holding company provides an additional layer. But the ongoing costs add up: annual fees for 6 entities (5 properties + 1 holding), registered agent fees, potentially 5 additional tax returns.
A simpler alternative for 5 properties: one or two LLCs (group properties by risk profile) plus a $3-5M umbrella insurance policy. This provides 90% of the protection at 30% of the cost. You can always restructure as your portfolio grows.