I ran a live quote test for a 3-bedroom, 2-bath rental in Austin, Texas, generating $60,000/year. I compared the two heavyweights in the STR insurance space: Proper Insurance (The Specialist) vs. Steadily (The Tech Broker). Here is the breakdown of price, speed, and exclusions.
Key Takeaways
- Proper is the “Tank”: It replaces your homeowners policy. Higher price, but covers everything (bed bugs, liquor, squats).
- Steadily is the “Speedboat”: They are a broker (selling carriers like Obie/Foremost). Fast quotes, cheaper, but coverage depends on which carrier they match you with.
- The “Squatter” Difference: Proper has specific language for “Wrongful Eviction” and income loss. Steadily’s policies vary by carrier.
- Price: Steadily came in 20% cheaper, but with a higher deductible and lower amenity liability limits.
The “Why” (The Trap)
The trap is “Apples to Oranges.”
Proper writes their own custom policy form (Lloyd’s of London). Steadily brokers policies from various carriers. When you buy from Steadily, you might get a “Foremost” landlord policy or a “National General” policy. You have to read the specific carrier’s fine print. Proper is consistent; Steadily varies.
The Investigation: I Called Them
- Proper Insurance: Quote: $2,800/year.
- Experience: 10-minute phone call required. Very knowledgeable agent.
- Key Feature: “Commercial Business Income” (Actual Loss Sustained) and no animal breed restrictions.
- Steadily: Quote: $2,150/year.
- Experience: 100% online, instant quote.
- Key Feature: Fast and cheap. The policy was a DP-3 (Landlord) with a Short-Term Rental endorsement.
- Gap: It had a “Vermin Exclusion” (no bed bugs) and lower limits for “Other Structures.”
Comparison Table: Proper vs. Steadily (2026 Data)
| Feature | Proper Insurance | Steadily (Broker) |
| Policy Type | Commercial Package | Varies (Usually DP-3) |
| Bed Bugs | Covered | Excluded (Usually) |
| Liquor Liability | Included | Optional/Excluded |
| Income Loss | Actual Loss Sustained | Fair Rental Value |
| Amenities (Bikes/Pools) | Included | Check Policy |
| Avg. Cost | | |
[IMAGE: Bar chart comparing premiums vs. coverage limits for Proper, Steadily, and Standard Homeowners]
Step-by-Step Action Plan
- Define Your Risk Tolerance: If this is your only asset and income source, pay for Proper. If you have 20 units and need to cut costs, Steadily is a great scalable option.
- Ask Steadily for the Carrier Name: Before buying, ask “Who is the underlying carrier?” (e.g., Obie, Aesir). Research that carrier’s reviews.
- Check the “Vacancy Clause”: Ask both: “If I have no bookings for 60 days, is coverage valid?” Proper usually says yes (commercial). Standard policies brokered by Steadily might say no.
- Bundle: Steadily is better at bundling (they can do your car/standard home too). Proper does one thing only.
FAQ
Is AirCover enough, so I can buy the cheapest policy?
No. AirCover is secondary. You need a primary policy that won’t cancel you for “commercial use.” Both Proper and Steadily solve that.
Does Steadily cover arbitrage?
Yes, they have products for non-owner hosts. Proper does as well.
Who pays claims faster?
Proper has in-house claims authority (faster). Steadily relies on the carrier (e.g., Nationwide/Foremost) to handle the claim (slower).