Checkout Shield vs Proper Insurance
Proper Insurance is a regulated short-term-rental insurance policy. Checkout Shield is the evidence layer that makes Proper Insurance, AirCover, and Resolution Center claims actually pay out. This is not a question of which one to buy. It is a question of why most professional hosts have both.
Last updated 2026-05-16
Quick verdict
The 30-second answer
Proper Insurance is a regulated commercial insurance policy underwritten for short-term rentals. It covers liability, lost income, and structural damage that AirCover excludes. It is the safety net under your business.
Checkout Shield is not insurance. It is the evidence system that makes claims succeed - whether you are filing with AirCover, Proper Insurance, or your standard homeowners policy. It captures GPS-verified, tamper-evident inspection reports before and after every stay.
The honest answer: if you own a serious short-term rental, you should carry both. Proper Insurance protects your business from catastrophic loss. Checkout Shield protects your routine damage claims from being denied for lack of proof.
Note: Checkout Shield and Proper Insurance solve different problems. Many hosts use both. This page explains where each one fits.
Side by side
Feature comparison
| Feature | Checkout Shield | Proper Insurance |
|---|---|---|
| Regulated insurance policy | ||
| General liability coverage | ||
| Lost income from unbookable nights | ||
| Structural building damage | ||
| Replaces standard homeowners gaps | ||
| Pre-stay inspection reports | ||
| Post-stay inspection reports | ||
| GPS-verified photos | ||
| Tamper-evident timestamps | ||
| Public verification link for AirCover | ||
| Side-by-side check-in / check-out comparison | ||
| Evidence that satisfies AirCover and a real insurer | ||
| Annual cost (typical) | $300 | $1,500-$3,000+ |
Choose by use case
When each one is the right call
Choose Checkout Shield when
Your claims keep getting denied for lack of evidence.
- You file AirCover claims and the guest disputes them.
- Your damage costs are typically $200 to $2,000 per incident - too small to claim on insurance, too large to absorb.
- You want one tool that protects every single turnover, not just catastrophic events.
- You manage one to a dozen properties and need an operational fix that pays for itself within the first denied claim.
Choose Proper Insurance when
You are exposed to liability or large structural risk.
- A guest could injure themselves at your property and sue.
- A kitchen fire or burst pipe could make the listing unbookable for weeks.
- Your homeowners or landlord policy excludes short-term rentals (most do).
- You have a sizeable mortgage or significant equity at stake.
Use both when
You run this as a real business.
- Proper Insurance covers catastrophic risk and liability.
- Checkout Shield covers the routine damage claims that happen every month.
- Both produce the evidence each respective claim process requires.
- Total annual cost is still less than a single mid-size denied claim.
Checkout Shield vs Proper Insurance FAQ
01Does Proper Insurance replace AirCover?
Does Proper Insurance replace AirCover?
No. AirCover is automatic on every Airbnb booking and is the first place to claim guest-caused damage. Proper Insurance covers what AirCover excludes - liability, lost income, structural damage, and damage from non-Airbnb guests. They work in tandem.
02Does Checkout Shield replace Proper Insurance?
Does Checkout Shield replace Proper Insurance?
No. Checkout Shield is an evidence tool, not an insurance policy. It makes claims succeed but cannot pay out on claims itself. If a guest sues you after slipping in the bathroom, only an insurance policy can defend you. If a guest stains your $900 sofa, Checkout Shield can prove they did it so AirCover or Proper Insurance pays.
03Which one do I buy first?
Which one do I buy first?
If your damage claims keep getting denied for lack of evidence, start with Checkout Shield - the impact is immediate and the cost is low. If you have no insurance beyond a standard homeowners policy and you are renting out a property worth more than $200K, get an STR-specific policy like Proper Insurance first.
04Will Proper Insurance pay a damage claim if I have a Checkout Shield report?
Will Proper Insurance pay a damage claim if I have a Checkout Shield report?
A documented before-and-after inspection report materially improves the speed and outcome of any insurance claim. Insurers reward clear chain of custody. We cannot speak for Proper Insurance specifically, but in our experience hosts with tamper-evident inspection reports settle faster regardless of which insurer they use.
05Is there overlap between Checkout Shield and Proper Insurance?
Is there overlap between Checkout Shield and Proper Insurance?
Minimal. Proper Insurance is the legal financial backstop. Checkout Shield is the evidence chain that lets you actually claim against backstops (whether AirCover, Proper, or a homeowners policy). The two products solve different problems in the same workflow.
06What about Slice, Allianz, or other STR insurers?
What about Slice, Allianz, or other STR insurers?
The same logic applies. Checkout Shield is the evidence layer underneath whichever STR insurance you carry. We are insurer-agnostic - any policy benefits from documented before-and-after inspection reports.
Your insurance is only as good as your evidence.
Proper Insurance covers what AirCover does not. Checkout Shield gives both of them the evidence they need to pay you. Start the free trial and seal your first inspection report today.
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