Proper Insurance Services Reviews 

Chelsey Helt from Proper was excellent to work with. She helped make a stressful situation flow as well as one could hope. Highly recommend!

⚠️ My Experience With Proper Insurance — Please Read Before You Buy

I wanted to share my recent experience with Proper Insurance, especially for anyone in the Airbnb or short-term rental community who might be considering them.

I would recommend looking somewhere else.

I’ve been trying to work with them on a simple quote for a while now, and the communication has been extremely poor. They are almost never available, and I was repeatedly told that the person I needed was “out to lunch.” This happened multiple times, with no one calling me back afterwards. I’ve escalated my concerns three times and still have not received a response from anyone.

For a company that supports customers across the entire country, their limited availability just doesn’t work. If basic questions and follow-ups are this hard to get, I can only imagine how difficult a claims process might be.

Sharing this in hopes it helps others who are weighing their insurance options for STRs.

Cade at Proper Insurance has provided me with both excellent service and coverage on both of my short term rental properties and made all claims easy and smooth. I highly recommend Cade and proper insurance to anyone looking for STR coverage.

Working with Matthew Stewart at Proper Insurance has been an outstanding experience from start to finish. Matthew was incredibly responsive, knowledgeable, and patient throughout my entire claims process. He made a stressful situation feel manageable by clearly explaining every step, answering all my questions, and advocating for me whenever needed.

It’s rare to find someone in the insurance world who genuinely cares, follows up consistently, and goes above and beyond — but Matthew did exactly that. My claim was handled efficiently, professionally, and with a level of support that exceeded my expectations.

I’m extremely grateful for his help and would highly recommend Matthew and Proper Insurance to anyone looking for dependable coverage and truly exceptional service.

If you are considering Proper Insurance, please read this first.
In my experience, this has been one of the most frustrating insurance companies I’ve ever dealt with — especially when it comes to filing a claim.

Instead of providing support during a difficult situation, they send extremely long, repetitive email requests that go in circles and never lead to meaningful progress. They ask for information that no other insurance carrier has ever required of me, including details that feel unnecessary, invasive, or irrelevant to resolving the claim. It often feels like the goal is not to help, but to exhaust the policyholder.

Their structure is also confusing — it’s not one cohesive company but a collection of different entities behind the scenes, which makes accountability difficult. In my experience, they seem far more focused on selling expensive policies than actually paying legitimate claims.

Property owners and vacation rental hosts, please read this before choosing Proper Insurance.
Based on my experience as a long-time short-term and mid-term rental operator, I found their claims process to be extremely difficult, time-consuming, and frustrating.

When I filed a claim, I received long, repetitive emails requesting information that felt excessive, irrelevant, or unnecessary for resolving the issue. The communication often went in circles, and despite providing detailed responses, the process never seemed to move forward. Instead of feeling supported, I felt overwhelmed, delayed, and discouraged.

Proper Insurance appears to operate through multiple entities and partners, which can make accountability unclear and the claims process harder to navigate. While their marketing targets vacation rental owners with promises of comprehensive protection, my personal experience was that their claims handling did not align with those expectations.

I’m sharing this so other homeowners, Airbnb hosts, VRBO hosts, and property managers can make informed decisions. In my opinion, there are other insurance carriers that offer clearer communication, more efficient claims handling, and far better support during stressful situations.

If you rely on your insurance company to step up during a crisis, carefully compare options before choosing Proper Insurance. My experience with their claims process was disappointing, exhausting, and not what I expected from a company advertising itself as a leader in short-term rental insurance.

We have used Cade Bachman at Proper Insurance for 6 years for our rental investment cabin near Helen GA..
We have always had good service from them and highly recommend

Proper insurance has done well by us. We had a rather large claim and they worked with us and guided us through the process. Now we have sold this property and the cancellation was easy.

Katie and Joseph worked with me deligently and with lots of patience to get me through this process. Of course, they have the best insurance for short term rentals available on the market. I highly recommend them!

Chelsey with proper insurance recently helped to guide us through a claim where guests found bugs at our air bnb property. This was such a difficult situation as we are take our cleaning protocols and business so seriously.

We reported the issue to Proper, our home insurance carrier, immediately and Chelsey was assigned and reached out by phone the same day to advise us to have an exterminator come out right away.

We had an exterminator visit right away and he issued the report. We sent this on along with proof of our lost income and Chelsey came through for us in less than a week to resolve the claim.

This was an already extremely stressful situation and Chelsey and Proper were amazing at helping us get through this so we could get back to business asap!

I worked with Alayna from Proper she was wonderful! It was my first time dealing with a claim and she made it a hassle less and an smooth process which I appreciated!

Mike has been responsive and thorough in his emails regarding coverage of our Airbnb property. Fortunately, I have not yet had to file a claim, but I feel fairly confident that if I do, I am in good hands.

I had an excellent experience with Zach (Claims Specialist) and Proper when handling my equipment breakdown claim. From the very beginning, they showed an impressive level of professionalism and care. They were patient in walking me through the process, always making sure that I understood what was needed and what the next steps would be. Their consistent follow-up gave me confidence that my claim was being managed thoroughly and efficiently.
What really stood out was their attentiveness—they never left me wondering about the status of my claim, and they made sure every detail was addressed in line with the policy. In the end, the claim was paid out exactly as expected, without unnecessary delays or surprise.

Worked with Elizabeth Young recently and had a fantastic experience, first claim I’ve had to submit while having multiple insurance policies through proper.

These people are deceptive!! They cover nothing but their prices keep going up. Terrible!!

Harold Helt is our hero!

Proper Insurance are backed by real people who are genuine, efficient and work to solve the issue(s) in real time and boy did Harold come through for us in our condo flood. From our first call, Harold melted our stress away, and dare to say even made it a pleasant experience. Harold guided us through our claim flawlessly, The repairs were coordinated & completed lightning fast with minimal disruptions - we are grateful. Harold Helt, with Proper Insurance Services, are rare as they actually provide exemplary service to their clients.

I was in a bind as a lesser insurance company told me that I had an active policy and then cancelled the night before my first guest arrives. Proper came to the rescue with a fair policy and great customer service, something that is is in short supply these days. Highly recommend.

You always get home insurance hoping you'll never have to use it. In our first year of owning a STR, we experienced moisture damage in our historic home. I want to thank Zach at Proper for being beyond helpful with our claim. Every time we asked for support, he provided above and beyond what we expected. Before we finished our first claim, another issue popped up and we were so much less stressed knowing we had Proper on our team. Both issues resolved and in the end our property is fixed up better than it was before, leaving our home worth more than when we started. I'll always recommend Proper.

I can’t say enough good things about my experience working with Elizabeth Young at Proper Insurance. She was responsive, professional, and incredibly helpful throughout the entire claims process.

What stood out most was how easy she made what could’ve been a stressful situation. She explained everything clearly, followed up promptly, and treated my concerns like they actually mattered. It’s rare to find that level of care and attention—especially in insurance.

I truly appreciated her support, and because of her, I would absolutely recommend Proper Insurance to others. Thank you, Elizabeth—you’re the real deal.

This was our first time contacting Proper Insurance and we are so happy with the service we received. Cayman was very helpful and knowledgeable. He took the time to really explain the policy and work with us. I would highly recommend Proper and Cayman :)

Thank you Cayman and all the folks at Proper for making my change in insurance companies so easy. I’ve never had such a quick response to questions and emails as I’ve experienced with Proper.