Search for “Proper vs Steadily” or “Steadily vs Obie” and most of what ranks was written by one of the three companies about the other two. That is not a neutral record. This comparison sticks to what can be verified from policy structure, public rating agencies, and each company’s own published materials, as of August 2026. Where a fact is not published, we say so instead of guessing.
The three companies are not three versions of the same product. They differ at the level of what kind of insurance contract you are buying, who stands behind it, and how it reaches you. Get those three questions right and the choice mostly makes itself.
The structural difference: commercial package vs dwelling fire
Proper Insurance sells one thing: a commercial package policy for short-term rentals, built around the Commercial General Liability (CGL) form that hotels use. Proper’s own materials lean hard on this point, and it is a real distinction, not marketing. A CGL form has no business-activity exclusion, which matters because renting to a stream of paying guests is a business activity, and business activity is exactly what standard homeowners and dwelling fire policies exclude. Proper pairs the liability form with commercial property coverage and business income coverage in a single package.
Steadily writes landlord insurance on standard dwelling fire forms, DP-1 and DP-3, with DP-3 as the primary product (Steadily). That is the same policy architecture described in our Texas landlord insurance guide: open-peril coverage on the structure, replacement cost on a DP-3, premises liability, and loss of rents. Steadily also states that it covers short-term rentals, including Airbnb and Vrbo properties, in all 50 states, positioning its product between a plain homeowners policy and a full commercial one.
Obie also sells dwelling fire policies, DP-1, DP-2, and DP-3, but Obie is not the insurer. It is a licensed broker and technology platform that quotes and places policies with partner carriers. The Coverage Cat review of Obie describes the product line as DP-form dwelling policies and notes that Obie will place hard-to-insure risks, including vacant properties and short-term rentals.
So the first sorting question is simple. Proper sells a commercial contract. Steadily and Obie sell personal-lines dwelling contracts, with Steadily acting mostly as the insurer and Obie acting as the storefront for other insurers.
Who actually underwrites each policy
This is where the marketing pages get quiet and the details matter, because the underwriter is who pays the claim.
Proper’s policy is underwritten by Lloyd’s of London and Concert Insurance Group, per Proper’s own FAQ, which cites AM Best ratings of A+ (Superior) for Lloyd’s and A- (Excellent) for Concert. Those are strong ratings from the main agency that grades insurer financial strength.
Steadily is the most complicated of the three. Founded in 2020, it operated first as an agency placing policies on partner carriers, then launched its own carrier, Steadily Insurance Company, in November 2024. That carrier is rated by Demotech, not AM Best. Steadily announced the launch rating as A (Exceptional) on Demotech’s Financial Stability Rating scale, and Demotech’s public company listing shows the rating affirmed in June 2026. Demotech is a legitimate rating agency, but its scale is not AM Best’s, and the two should not be conflated. Steadily also still places policies through its agency arm with outside carriers, so the underwriter named on a Steadily quote can vary; an AM Best rating disclosure for Obsidian Insurance Company hosted on Steadily’s own servers identifies one such partner. The practical takeaway: read the declarations page to see whose paper you are on.
Obie has no rating because it is not a carrier. Independent reviews, including Coverage Cat’s, report that Obie’s partner carriers include American National Lloyds Insurance Company and Accelerant Specialty Insurance Company, and that all of Obie’s partner carriers hold AM Best ratings of A- or higher. One caveat from the same review: some Obie placements are on non-admitted paper in certain states, which means no state guaranty fund protection if the carrier fails. That is a normal trade-off for hard-to-place properties, but you should know when it applies to yours.
Short-term vs long-term rental fit
For a dedicated short-term rental, the exposure is closer to a small hotel than to a leased house: a new occupant every few nights, amenities like pools and hot tubs, guest injuries on and off premises, and revenue that stops when the property goes offline. Proper’s product was designed for exactly this, with commercial liability starting at $1 million per occurrence and coverage for guest-caused damage. Steadily and Obie both state they will cover short-term rentals on DP-based policies, which can be a workable and often simpler purchase, but the burden is on the buyer to confirm how the policy handles business activity and guest damage, in writing, before binding. Our roundup of the best short-term rental insurance in Texas goes deeper on that market segment.
For a conventional long-term rental with a 12-month lease, a commercial package is more policy than the risk requires. This is Steadily’s and Obie’s home turf: a DP-3 with replacement cost, loss of rents, and premises liability is the standard structure, and both companies quote it online in minutes.
Loss-of-income terms
The differences here are structural, not cosmetic. Proper’s site describes business income coverage with no time limit when a covered claim takes the property out of service. DP-based policies handle the same risk as “loss of rents” coverage, which is capped, typically in months or as a percentage of the dwelling limit, and on a DP-1 the cap reduces the dwelling limit itself. Obie’s materials describe loss-of-rent coverage that pays when the property is uninhabitable from a covered loss, but the duration terms are not published; that is a question for the quote. For a high-revenue vacation rental, the difference between capped and uncapped income coverage can be the largest dollar difference among the three.
One more term worth asking about on any of the three: what triggers the income coverage. All of these policies pay lost income only after a covered property loss, not for a booking slump, a platform suspension, or a city permit dispute. An owner who reads “no time limit” as “covers any lost revenue” is reading it wrong, and that misreading is common enough that it belongs in the comparison.
Liability limits
Proper: $1 million per occurrence standard, with an option to increase to $2 million, per its FAQ. Steadily: its liability coverage page describes limits from $300,000 to $2 million per occurrence, written into every landlord policy. Obie: reviews report standard liability at $1 million to $2 million. On limits alone the three overlap heavily; the difference is the form the liability is written on, not the number.
States and how each one sells
All three operate in all 50 states and Washington, DC (Steadily). Distribution differs. Proper sells direct through its own in-house agents who work only short-term rental risk, and also appoints independent brokers (Proper). Steadily sells direct online and by phone, and also appoints independent agents. Obie sells three ways: direct through its online platform, through independent agents, and embedded inside partner platforms via API, which is why an Obie quote sometimes appears inside other landlord software you already use.
What each one does not publish
None of the three publishes premium tables, so any article quoting a “typical Proper premium” is quoting a single data point or inventing one. Proper does not offer a product for pure long-term rentals. Steadily’s own carrier is young, carries a Demotech rather than AM Best rating, and the underwriter on your policy can vary by state and property. Obie does not disclose on its own site which carrier you will land with until you quote, and some placements are non-admitted. These are limitations, not disqualifiers, but a vendor-written comparison will not tell you the ones that apply to its author.
Who fits whom
Skip the winner talk. Match the structure to the property.
A dedicated short-term rental with real revenue — full-time Airbnb or Vrbo, pool or hot tub, meaningful nightly income — fits Proper’s commercial package best on structure: no business-activity exclusion, uncapped business income, and hotel-style liability. Quote Steadily against it anyway, because a DP-based STR policy may price differently and the gap is worth knowing.
A long-term rental with a 12-month lease fits Steadily or Obie. Proper is not built for it. Between the two, Steadily is the closer thing to a single insurer relationship; Obie is a shopping mechanism across carriers, which earns its keep on properties one carrier might decline.
A hard-to-place property — vacant, mid-renovation, mixed-use, or a portfolio one carrier will not take whole — plays to Obie’s broker model, with the non-admitted caveat checked on each quote.
An owner comparing against occupying the home should note that none of these products replaces homeowners insurance; for that baseline, see our guide to Texas homeowners insurance costs.
Whichever direction fits, get the competing quote anyway. All three quote fast, none publishes prices, and the declarations page — the form, the limits, and the carrier actually named on it — is the only comparison that pays a claim.