Connecting with your guest as a remote superhost with Tammi Sims
Some of the links mentioned are affiliate links. if you choose to make a purchase, I may earn a commission. Commissions come at no additional cost to you.

On today’s episode, I’m doing something new. Yes, we’re trying different things here at The Hosting Journey podcast. This week’s episode is:

“What Would Evelyn Do:

Should I Allow This Guest in My Home?”

My Facebook Group The Hosting Journey, which is now over 2,400 members strong… By the way, are you part of that group? I hope so, but if you’re not and you want to be, all you have to do is go to The Hosting It’s a fun group, very supportive and full of information.

As I was saying, members of the Facebook group started this, “What Would Evelyn Do?” question series. So, I decided to share the questions people posted, share the community’s answers, and then share my answer for “What would Evelyn ACTUALLY do”, with you, my dear listeners…

I really do think that we ALL work best when we’re able to listen to each other's ideas, suggestions, and points of view when we’re able to collect them all and then come to our own very best conclusion. As Tina Turner would say, “Simply the best!.”

Shery’ls Question: Should I Allow This Guest in My Home?

The first question comes from Sheryl, a Superhost from Massachusetts. She is a seasoned host of over 3 years. Nonetheless, she wanted our opinion about this situation.


Please note guests names and reviews have been edited.

Sheryl’s question was: “What would Evelyn do? I got this guest inquiry, and of course, I looked at their past reviews and saw this… What to do? Seems like trouble, although it's only a two-day booking. I've attached her inquiry and terrible review.”

Here is the Inquiry from the Guest:

“My 24 yo son T. is a groom for a close family friend in a weekend in a nearby town, so we’re both traveling from out of state to visit. We’ll be in your area for 2 days.”

And here is the Negative Review for Sheryl’s Inquiring Guest:

“I found the guest to be a difficult guest. I felt challenged by them at several points, and I would not host them again or recommend them. For example, I like to offer guests early check-ins or late check-outs whenever timing allows. I offered this guest early check-in as the house had been cleaned/prepped a day earlier. The guest asked for late check-out, but we had another guest coming in a few hours and we needed every minute between guests. The guests became pushy and felt we didn’t need that much time between guests (we did!). Also, upfront they asked about having the cleaning fee and Airbnb service fee refunded, as well as security deposit. Guest also seemed put upon about our request for guests to put used towels in the tub wash their dishes and put their trash in the bins. I’ve had over 400 friendly… 

You get the idea…

The guest had 20 reviews; three were negative. Out of the three negative reviews, Sheryl posted only this one.

Our Answers:

Reviews. As hosts, they’re sometimes hard to read and hard to write. But that’s for another upcoming episode, which I know I’ve been promising you. It’s in the works. The hosting community asked about the other reviews, but we didn’t get to see them.

Here are three of many comments from the hosting community:

  • Decline!
  • This is an appropriate time to decline.
  • If someone asks up front for a discount, I immediately decline them. Nothing but potential trouble.

Now, what would I do? It depends on the other reviews. As a guest, she had 20 reviews, and only 3 were negative.

What were the other 2 negative reviews about? And how were the other 17 reviews? We didn’t have this information. All we had was the inquiry and this one negative review. The host asking the question had other information we didn’t have.

My Reasoning:

So, based on this one review and this limited information, I probably would have accepted this guest.

It was a very short booking; two days. The inquiry was good. The guest provided all the information I’m looking for in an inquiry.

  • The reason for the visit,
  • An introduction,
  • And the number of people.

The guest didn’t ask for a discount or early check-in or any of the other issues the other hosts had.

In my communication, I would have mentioned the negative reviews and said…“Hi, it looks like you have these reviews that give me pause about accepting you in my home. Can we talk about them?”

Of course, depending on how that exchange of communication goes with the guest, I would then make my final decision as to whether to accept them or not.

In Episode 8, Connecting with your Guest as a Remote Superhost with Tammi Sims, Tammi spoke with us about how she specifically communicates with guests. Listen to this episode to get ideas on to how to ask the right questions to your guests and how to get them to open up to you. You don’t have to be a remote host to get tips from it, trust me. This episode was full of hosting nuggets.


Sheryl’s Decision:

“I want to decline, but do I need to give them a reason…as you can tell, three years hosting, I've never had to decline! This is new ground for me. Just worried that I'll go down in search priority, they'll block the days, or I'll get a mark on my record.”

How to Decline a Booking Inquiry:

From Airbnb’s website

You can decline any booking inquiries or reservations that you can’t accommodate, but you should do so within 24 hours. Whether you accept or decline, the amount of time it takes you to respond to requests is factored into your response rate.

When you decline a reservation request, you can choose to keep the calendar dates blocked or make them available for someone else to book. Update your calendar regularly so you only receive reservation requests for when you're able to host.

So remember to do it within those 24 hours.

Also from the Airbnb site:

Declining an individual reservation request won't negatively impact your listing's placement in search results; however, if you decline many or most reservation requests, your search result placement may be negatively impacted.

Of course, Airbnb doesn’t tell us what “declining many” means. What is that magical number of many? If you know the magical number of “many,” please let me know. because…

Inquiring minds want to know.

Lionel’s Question:

Do I Charge a Guest Security Deposit for Damages?

Lionel has a vacation rental in Hawaii, but he lives in Portland. He is a remote host and has been in vacation rental world for less than a year. Lionel is actually using the VRBO platform and not yet on Airbnb. Yes, my dear hosts, I don’t discriminate. Everyone is welcome at The Hosting Journey.

Unfortunately, or fortunately, Lionel isn’t on our facebook group, so he didn’t ask this question to our community, he came directly to me.



Here was Lione’s question:

“A recent guest destroyed one of our bicycle’s rims. The cost to repair was $70. Do I take this from his security deposit or write it off as a loss?”

Good question, Lionel.

Broken items from guests. We all have them. Whether it's makeup stains on our towels, broken plates or in this case, a destroyed bicycle rim…. When is it a good time to go after the security deposit? You do have a security deposit, right?

For things like towels, broken glasses, plates, and small items, I don’t bother charging guests. I call this “The Cost of Doing Business.”

Of course, there are exceptions.

  • Did they use the plates and glasses for target practice?
  • Use ALL the towels to remove their ZOMBIE make-up from their Comic con convention?
  • Or didn’t tell me that they broke my grandma’s vase and just HID the pieces in the closet under the towels?

Because if that’s the case, then my “Hey, it’s business” and my zen-like personality go out the window. If it’s done with certain intention and dishonesty, then I’ll go after the deposit and write them a negative review. Oh yeah, don’t make me go all Puerto Rican on you… It’s not pretty. Well, at least now you know.

But if they tell me, I removed my make-up with your white towels and stained them, I will sigh heavily. Repeat sigh… Wonder, how could they not see the make-up wipes? Then, I’ll say it’s fine.

You see, it all depends on how a guest behaves. Honesty can equal a positive review, even when sometimes a negative thing happens. I once had a guest who told me they put a hole through the closet door and to use the security deposit to repair it. I know you want to know how they made a hole through the closet door. You’re curious like that. Not nosey.

Well, I’m not one to gossip, but they said they were leaning against it with a chair. That’s it. Yep, that’s it. No big fight or crazy party. I made a claim through Airbnb and got it fixed, Easy peasy. You see how amazing it is to deal with adults.

My Answer to Lionel’s Question:

In Lionel’s case, he was told by a guest that one of his bikes was broken. He wasn’t sure who did it. He had an idea but he didn’t have 100% proof. I was sorry to inform him that he needed to write it off as a loss. You just can’t go back to a past guest and say without proof, “Hey, I think you broke my bike”… or you did this or that.

In the future, Lionel can have his cleaning crew double check that all equipment is in working order. Yes, it’s one more item for them to do when they’re cleaning and transition from one guest to the next, but it’s a very valuable and necessary money-saving step.

Even as a live-in host, it’s hard to keep track of your home, especially during the high season, when guests are coming in and out, out and in… Sometimes turnovers are on the same day… and it’s just difficult to keep track.

As a remote host, it’s even harder. You have to depend on your amazing crew. And you better have an amazing, top notch crew taking care of your property because if you don’t, before you know it, you might not have a business.

How to Protect Yourself as a Remote Host:

I recommend that you use an app called Properly, which you have heard me mention in the past. With Properly you can send cleaning instructions to your housekeeper or cleaning staff from anywhere in the world… this way everything is picture perfect when your guests open the door. You make visual checklists, using your listing photos that your staff follows, so you can add things like, “check equipment for any damages.”

But even better than that, your staff takes photos of any damages, and you can also ask them to take photos of their finished work. So you can see your place before your guests arrive. And the proof is in the photos. If you want to try Properly, be sure to use my link to sign up for your free 14-day trial at:

Note, this is an affiliate link, which means that if you sign up, I may earn a commission, at no additional cost to you. I’ll use the money to replace those stained towels. I promise.

How to Make an Airbnb Claim Against Security Deposit:

Now, if Lionel was on Airbnb, which he isn’t…YET… I’ll be bringing him over soon. I promise….and he was going to make a claim for security deposit, these are the steps he would take.

Let’s first talk how to add a security deposit. From the Airbnb website:

How does Airbnb handle security deposits?

Hosts can add a security deposit to their listing, as long as they add it before a reservation is booked.

To add or edit a security deposit in your pricing settings:

  1. Go to Manage Listings on
  2. Select the listing you want to edit
  3. Select Pricing settings in the upper right-hand corner
  4. Under Extra charges and currency, check the box next to Security deposit
  5. Enter an amount between $100 and $5,000 USD

The security deposit only applies to reservations booked after the changes are made; they don't retroactively apply to existing reservations. Security deposits can't be handled off-site in cash, as off-site payments are a violation of our terms.

Security deposits CAN’T be handled off-site in cash, as off-site payments are a violation of our terms.

What do I do if my guest breaks something in my place?

If you need to make a claim on your security deposit, you can do so in the Resolution Center within 14 days of your guest’s check out date or before the next guest checks in, whichever is earlier.

To make a claim on a security deposit:

  1. Go to the Resolution Center on
  2. Choose the relevant reservation
  3. Under Select a reason, select Request compensation for damages
  4. Click Continue to submit details about the damages and associated costs on the next page

If your guest agrees to the amount you requested, we'll send you a payout between 5 to 7 business days.

If your guest declines or doesn't respond within 72 hours, click Involve Airbnb in your Resolution Center case. If we require additional documentation, you'll have 72 hours to provide this documentation.

Most security deposit claims will be resolved within one week. We'll make sure you and your guest are represented fairly, and if we determine you're owed money, we'll send it to you in a separate payout.

In any case, we'll make sure you and your host are represented fairly and gather any details and documentation needed to reach a resolution. Most security deposit claims will be resolved within one week.

Unfortunately, this is one of the biggest frustrations from hosts and vacation rental owners using Airbnb. On other vacation rental sites, an owner collects a deposit, and if there is a damage they just deduct it. They deal with the guest directly.

With Airbnb, they decide if we, the host, have the right to collect for our damages and how much. It’s very frustrating. In many cases, hosts feel that Airbnb favors the guests.

Fair or not fair, it’s the system they have, for now.

So, What Did Lionel do?

He wrote it off as a loss, but now his bikes are locked. The guests are welcome to use them, but they have to sign an agreement and assume responsibility. Only then will he give them the combination to the lock. Officer Lionel took control.

In addition, the cleaning person knows who is using the bikes and will check them for any damages. This way, Lionel has a bit more control over who is using his equipment, too.

These are lessons you learn by trial and error or by listening to us and collecting ideas, suggestions, and points of views to make your very own best conclusion.

Your Questions:

I hope you enjoyed this Episode, “What Would Evelyn Do: Should I allow this Guest in my home?” I get questions all the time, and I want you to know my logic and thought process on how I come up with my answers.

So, go ahead and ask me a question, you never know I might use it in an upcoming episode.

Though my answers might at times go against the grain, ALWAYS remember, at the end of the day… It’s your home, and you have the final say on what works and what is most comfortable for YOU.



Some of the links mentioned are affiliate links. if you choose to make a purchase, I may earn a commission. Commissions come at no additional cost to you.


Properly is a change over management tool for your vacation rental that lets you make interactive visual checklists, schedule your service providers, connect to your listing platforms, and organize other change over services.

Want to try the Properly app to find service providers and get perfect turnovers every time? Get a free 14-day trial at:

PS: Want more…

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