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The Roof Is Where the Two Exits Stop Agreeing
Oklahoma homeowners pay $5,298 a year to insure a house, the highest average of any state and 121% above the national figure. Tulsa sits inside that number. AirDNA scores the same city 97 out of 100, on 2,005 listings running 57% occupancy at a $160 average rate. Both facts describe the same houses. One of them shows up in a rentalizer.
On a composite 1960s three-bedroom bought at $152,000, the host exit carries a $2,700 policy and the lease exit carries $1,450 on the same roof under the same hail. The $104 a month between them is not renegotiable after closing. It is set by the roof, and the roof is bought at the offer.
Carriers now flag asphalt shingles at 15 years on new business, and at 20 many swap replacement cost for actual cash value. So we'd price the roof ahead of the kitchen. Buy a four-year roof and both exits stay open. An eighteen-year roof is a $13,000 tear-off, which a resale buyer forgives and a carrier does not.
The upgrades sold on top of it are a separate question. Class 4 impact-resistant shingles add roughly $2,500 and earn a 20% credit against the wind-and-hail portion of the premium. State law encourages the credit without fixing a number. On a worked $16,000 replacement, the upcharge clears in year eight. The hold ends by three.
What we'd do: make roof age a bid condition in hail country. Ten at the offer is inside fifteen at the exit, so the host policy stays writable at replacement cost through the hold. Past fifteen, the seller re-roofs or the tear-off comes off the price. The same roof is the fallback to the $1,214 lease. Everything else here is negotiable. The roof is not.
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Hosting nets $1,779 a month against $1,214 on a lease, both self-managed, both carrying a maintenance reserve, neither carrying debt. Strip the insurance differential out and the edge is $669. The host policy takes $104 of it back. The ADR runs above the citywide blend, $175 and 55% against AirDNA's $160 and 57%. None of this is a live listing. Redfin's and Zumper's September Tulsa medians carry the buy and the lease, and both premiums are modeled inside published Oklahoma ranges.
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A flip changes insurance status more than once before it earns a dollar. Vacant and under construction it needs builder's risk, which most homeowners carriers will not write and many landlord policies exclude outright. Finished and hosted it needs short-term rental coverage, or a landlord policy if it goes to a lease. Steadily writes all three across 50 states, quotes online in minutes, and converts the builder's risk policy to a landlord or STR policy when the work ends, so the house is not re-underwritten at the handover.
Steadily does not carry the risk. It places quotes through a network that includes non-admitted surplus-lines carriers, which are not backed by state guaranty funds if the carrier fails. Ask which carrier the quote sits with, and whether it is admitted, before binding.
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01 — Chincoteague's council approved a short-term rental ordinance September 8. From January 1 the island's roughly 750 rentals will need two-night minimum stays and one off-street parking space for every two guests, with occupancy limits attached. A sleeps-ten house on a two-car pad is a sleeps-four house until someone pours concrete. Source→
02 — Airbnb began pushing a "direct booking link" toggle to selected hosts in late August. Traffic arriving through the host's own link bills at 6% or 10% rather than the flat 15.5%. Airbnb still processes the payment and keeps the guest's details. The host supplies the marketing and rents the discount back. Source→
03 — A July audit found 8% of Killeen's short-term rental operators were collecting the city's hotel occupancy tax. The program booked $105,216 in FY2025 against a projection near $700,000. Council took it up September 15. A gap that wide gets closed by a contractor with a data feed and a back-tax bill. Source→
Worth Watching — Airbnb's hotel inventory is growing at more than double the rate of the rest of its business, concentrated in the urban markets regulation already thinned. The exposure sits in one-bedroom listings at $127 to $219 a night. Three-bedroom houses compete with nobody new. Source→
What does insurance actually run where you buy? Reply and tell us — or forward this to someone who never checked.
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The flip side of short-term rentals BUY IT · FLIP IT · HOST IT |
