Insurance requirements as you scale: protecting a multi-property portfolio

Category: Multi-Property & Scaling

By: Tasha Williams

Posted: 2025-12-21T13:57:56.527Z

I'm at 5 properties and realizing my insurance situation is a patchwork of different policies from different providers. Some are covered by standard landlord policies, one has STR-specific insurance, and one I'm not sure is properly covered at all. How should insurance be structured for a 5+ property STR portfolio?

Reply by Tony Russo:

Insurance is the #1 thing hosts underestimate when scaling. Here's the proper framework: **Individual property coverage (required for each property):** 1. **Dwelling/property insurance** — Covers the structure and your furnishings/contents - Must be an STR-specific or landlord policy (standard homeowner's voids if you STR) - Providers: Steadily (https://steadily.com), Proper Insurance, CBIZ - Coverage: Replacement cost of structure + $50K-100K contents 2. **Liability insurance** — Covers guest injuries and lawsuits - Minimum $1M per occurrence - Included in most STR property policies - Stack with AirCover but NEVER rely on AirCover alone 3. **Loss of income coverage** — Covers lost revenue if property is damaged and can't host - Critical for STR where you lose bookings during repairs - Usually an add-on to property policy **Portfolio-level coverage (for 3+ properties):** 4. **Commercial umbrella policy** — $1M-5M additional liability coverage that sits on TOP of your individual property policies - Cost: $500-1,500/year for $1-2M umbrella - Covers lawsuits that exceed individual policy limits - ESSENTIAL at 5+ properties — your exposure compounds with each unit 5. **Workers' compensation** — if you have ANY employees (cleaners on payroll, maintenance staff) - Required by law in most states - Protects you if a cleaner is injured at your property 6. **Professional liability (E&O)** — if you co-host or manage other people's properties - Covers claims of negligence in your management services **Per-reservation coverage (supplemental):** 7. **Safely** (https://safely.com) — per-reservation guest screening + damage protection + liability - Great supplemental layer on top of your annual policies - $8-15 per reservation **My recommendation for 5 properties:** - Steadily annual policy per property (~$1,500-2,500 each = $7,500-12,500/year) - Commercial umbrella: $2M coverage (~$1,000/year) - Safely per-reservation: (~$2,500/year total across all properties) - **Total insurance budget: ~$11,000-16,000/year** (about 5-7% of gross revenue) This sounds expensive, but ONE major lawsuit without proper coverage could cost $100K+. Insurance is the cost of protecting your entire portfolio.

Reply by Camille Dubois:

I'll add: get ALL your policies from the same provider if possible. When you have a claim that touches multiple policies (e.g., guest gets injured AND their claim exceeds your property liability), having the same insurer avoids finger-pointing between companies about who pays what. Steadily and Proper Insurance both offer portfolio-level packages where they bundle property coverage + umbrella + loss of income across all your units. The bundle pricing is usually 10-15% cheaper than individual policies.