Running a short-term rental means juggling guest communications, cleaning schedules, and making sure every stay is five-star worthy. But what about your bookkeeping?

As hosts we are amazing at managing the minutiae and ensuring guests experience nothing less than a picture-perfect stay. But, many of us could improve our overall approach to save ourselves from future headaches.

Commingled Expenses
Since the nature of our business often necessitates personal and business errands happening at the same time, it’s important to remember not to commingle expenses. This means personal expenses should be kept separate from rental property’s expenses when we make purchases. Be sure to save receipts so later we can provide proof of the expense.

Mileage Deductions
All this running around usually involves a car. Be sure to track your mileage so you can deduct them as a business expense on your annual income tax return. I used to keep a simple form in the car and I noted miles out, where I went, and the miles when I returned. When the log filled up, I transferred it to a spreadsheet. You could also use a simple, online Google Form or even an app to track your miles.

Track Your Data
Speaking of relying upon online tools to track your data, you should be careful not to rely solely upon an online platform like Airbnb to track this info. Opt for an accounting system of some sort to ensure you retain the data you need for your business in the future.

Keeping track of all of these expenses, deductions, and tax documents can feel overwhelming, until you learn a few smart strategies.

On April 17th, Host2Host is bringing in professional bookkeepers who specialize in working with hosts like you. They’ll share practical tips to streamline your financial records, avoid common pitfalls, and make tax time less stressful. Whether you’re just starting or looking to refine your process, this meetup will provide valuable, actionable insights.

Join us at our April meetup and get your financial house in order!

I’ll preface the summarized ideas below with the fact that I’m fascinated by little details that niche communities uncover in collaborative settings.  I love the unobvious, unpublished ideas that are often brought about in conversations with industry experts and fellow hosts. One person’s question brings about another person’s epiphany, which brings out another person’s curiosity.

Whether virtual or in-person, events with Host2Host are chock full of conversations like this. Recently Host2Host members gathered with 3 professionals from 3 alternative platforms: HostShare, Radious, and PadSplit. Here are a few "light bulb" moments I had about each platform. But I promise there’s more if you consider watching the entire conversation, especially if you’ve never heard of these alternative platforms!

HostShare offers hosts opportunities to book properties up to 5 days in advance for up to 21 nights of free accommodations annually within the HostShare network. Hosts only pay cleaning fees, avoiding nightly rates, platform fees, or taxes.

While the “free” nights sound appealing, I also was super reluctant to think that a 5 day advance booking window is sufficient time to plan around work, family, and life. Anthony then pointed out something entirely unobvious to me: simply consider booking a hotel well in advance because most are refundable until the day before check-in anyway. Then shop a HostShare stay as travel window approaches closer. This immediately addressed my anxiety if a HostShare stay isn’t available during the desired travel window. To me, this is an unobvious strategy just isn't something HostShare could publish, but it absolutely made me reconsider the platform. Hosts hosting hosts!

Radious may be much more compatible with HOA’s and neighborly concerns about short term rentals than I realized, mainly parking and noise concerns. It was unobvious to me that parking is much less of a concern because Radious guests are not overnight guests, they are generally only on-property during business hours.  Amina pointed out, funny enough, Radious guests and neighbors become like two ships passing each other in the day. Potentially much less traffic impact than overnight guests. Again, maybe obvious to others, but since Radious doesn’t host overnight guests, Radious hosts can often avoid the need for short term rental permits in certain markets. 

Padsplit could be summarized as a platform for mid-term, co-living room rental stays. For hosts and investors, renting a furnished home by the room may offer an opportunity for greater cashflow than a traditional long term rental.

HOWEVER, my big unobvious “aha!” moment was realizing that given the nature of multiple turns and staggered lengths of stay among multiple rooms, hosts and home owners have much more frequent and legal access to their properties. Hosts typically cannot enter the home while guests occupy the property. However, with individual room leases, it seems homeowners can indeed enter common areas of the home and unoccupied rooms in the home, be it for cleanings, maintenance etc. This probably warrants further consideration but this struck me as an unobvious, unpublished benefit for homeowners to feel at ease that they can enter their own property, especially when compared to a traditional long term rental.

Watch the conversation on Youtube to discover your own unobvious moments!

This month the light in the world shone just a little dimmer after our bright, shining star – one of Host2Host’s founding members, former Executive Director and indefatigable leader passed away after a long and courageous battle with cancer. 

If you had the opportunity to know Jill, you know that she was a true force to be reckoned with, a generous leader, and an inspiration to so many. Her contributions to creating a strong and lasting foundation for Host2Host cannot be overstated. In her honor, our Board of Directors has created the Jill Palamountain Memorial Fund and will be seeding it with $500. Money collected will be donated to Portland Youth Philharmonic, a non-profit that Jill was very supportive of. If you would like to contribute to the fund, please make a donation here. Our donation will be made based on all the funds we have collected by March 31, 2025.

A celebration of life remembrance is in the works. We’ll send out more information about that when we have it. If you have a moment or two to spare a thought for her husband Michael and son Forrest, I know they would appreciate feeling the love at such an incredibly difficult time.

Email Charity for their contact details if you would like the opportunity to reach out directly or if you have questions about contributing towards the memorial fund.

Say the things you need to say and hug your loved ones extra hard today. Thank you for being a part of our community.

Remembering Jill Palamountain
By Debi & Rob Hertert, founding members of Host2Host

“OMG! This actually blows me away, Jill! I’m bowing deeply to you. I knew we have a wonderful team of people, but, forgive me if I wax hyperbolic, you’re a perfect example of why we, as an organization, will thrive. Thank you a million times.” 

This was Alan Colley’s reaction to Jill’s draft of the very first Host2Host newsletter for April, 2018. How many times did Jill “wow” us with her ability to write, guide, organize, nudge, and plan? And all of us who worked with her must smile remembering her signature, gentle nudge in meetings: “so how can we move this along?” 

The H2H Board hired Jill as our Executive Director and she immediately impressed the Board with her ability to take charge without stepping on toes. She assumed responsibility for so many aspects of the new organization, making it clear that choosing her for the job would prove to be instrumental for the young organization.

Jill had a combination of skills and personality traits that made it almost impossible not to like her and admire her ability to organize, plan and collaborate. She didn’t seek the spotlight, but didn’t shrink back when it was needed. Her optimism, sense of humor, great smile, patience and fun energy made her great to work with -but-  it had to end in some forward progress :) She never missed a deadline. She was the epitome of “work in the sense of joyously moving forward.” (Abraham Hicks)

Jill will be sorely missed by all who knew her. Host2Host’s success is in large part due to her stewardship. She always found the best in us, offering her sweet smile and soft encouragement. 

We were blessed to have you with us, Jill.  You are dearly missed. Thank you from our hearts, and God Speed.

For years, Airbnb and Vrbo have been the dominant platforms for short-term rental hosts, providing valuable opportunities to generate income and connect with travelers. However, as the home-sharing landscape evolves, an increasing number of alternative platforms have emerged, catering to diverse needs and preferences. 

Why Consider Alternative Home-Sharing Platforms?

1. PadSplit – Affordable Housing with a Purpose

2. Hostshare – A Community for Hosts, by Hosts

3. People Like Us – The Home Exchange Experience

4. Furnished Finder – Ideal for Traveling Professionals

5. Kindred – Reciprocal Hosting for Travelers

6. Becoming rentABLE – Aggregator for Disability-Friendly Travel

7. Radious – Fill the Gaps with Day-Time Professional Rentals

Choosing the Right Platform for You

As climate change intensifies, so too do the risks faced by homeowners, especially in states like Oregon that are prone to wildfires, storms, and extreme weather events. While many of us in the Portland area are aware of the rising temperatures and unpredictable weather patterns, it's becoming increasingly clear that these changes will have lasting consequences on insurance policies, particularly for those of us in the short-term rental community.

In recent years, California has been at the forefront of a troubling trend: as wildfires become more frequent and severe, many homeowners have seen their insurance canceled or their premiums skyrocket. While Oregon has thus far been spared the worst of these effects, experts predict it is only a matter of time before these issues impact our state as well. This is already being reflected in the growing difficulty for homeowners in high-risk areas to obtain affordable insurance coverage.

For short-term rental hosts, the stakes are even higher. If you're renting out your property or planning to do so, understanding how climate change is impacting insurability is essential for protecting your investment and ensuring your property is covered in the event of a disaster.
 

What’s Happening in the Insurance Industry?

As wildfires, hurricanes, and extreme weather events become more frequent, many insurance companies are rethinking their approach to coverage in high-risk areas. Some companies are reducing their exposure to fire-prone zones, while others are pulling out entirely. This means fewer providers are willing to offer coverage, and those that do often increase premiums or impose stricter requirements.

In Oregon, we are already seeing signs that insurers may begin to pull back from higher-risk regions, particularly in areas close to forests or coastal zones. This could put short-term rental hosts in a difficult position when it comes to obtaining the right insurance coverage at an affordable price.

Preparing for the Future: How Hosts Can Protect Themselves

• Review Your Policy: Make sure you have an up-to-date understanding of your current insurance coverage. Does it cover natural disasters like wildfires or floods? Are there exclusions for specific weather-related events? Knowing exactly what’s covered—and what’s not—is the first step in protecting your property.
• Mitigate Risk: Many insurers are more likely to cover homes that have taken steps to reduce risk. Installing fire-resistant materials, maintaining defensible space around your property, and implementing water protection measures can help reduce your exposure to climate-related damage and improve your insurability.
• Stay Informed: The insurance landscape is evolving quickly, and staying informed about the latest trends in climate change, insurance policies, and regional risks is key.

Join Us for Navigating Insurance in the Age of Climate Change

• The latest trends in insurance cancellations and premium increases
• How climate change is shaping the future of insurability in Oregon
• Practical tips for reducing your exposure to climate risks
• What to look for in an insurance policy as a short-term rental host

Thanks to the connections made by Host2Host founding member and Becoming rentABLE Board Member, Debi Hertert, we were honored to welcome Chief Energy Officer and founder Lorraine Woodward with Becoming rentABLE to our January meetup. In this enlivening conversation, we learned more about how to create spaces that are more welcoming to a broad set of travelers increasing the amount of potential renters that will be attracted to your listing.

In the US alone, the number of travelers with disabilities is on the rise with 27% or around 71 million potential guests expected to grow in coming years as Baby Boomers continue to age. Studies show there are not nearly enough accessible units for the number of travelers who are ready to explore the world. By making very small changes or even just by adequately advertising your listing, you can tap into a growing market and stay ahead of the curve.

When you're ready to learn more, check out our Youtube recording and head over to Becoming rentABLE to signup for one year of FREE CERTIFICATION and discounted consultation fees just for being a Host2Host newsletter subscriber (CODE: H2HFREEYEAR). Don't forget to like and subscribe to our Youtube channel.

Becoming rentABLE explains 63 different ways to be an accessible property. Let's expand travels options for everyone!