The big meetup event in November was the Tax Time Gotchas panel discussion with local tax preparers! We’ve been offering this opportunity for hosts in the community to connect with expert advisors for several years and this one did not disappoint!  Hosted by Host2Host founding member and Education Chair, Debi Hertert and H2H Board Member, Anthony Rallo, this event provided a chance for tax advisors, Stephanie Solomon of Block Advisors, Eve Davis or In or Out Tax Services, and Jaydra Perfetti of Paper Investigators to offer specific and timely information about changes in tax law.    Once the speakers were done, hosts on the call were invited to ask questions about their specific tax situations. Members - don't miss the awesome information exchanged in the chat and the special offers for the Host2Host community! If you weren’t able to attend but want to check out the information that was exchanged, watch it on our Youtube channel at your convenience.

This upcoming year brings a lot of changes to our organization of community-focused hosts.

We are excited to welcome Kristy Olsen to the Board of Directors. A long-time short-term rental host with experience managing traditional rentals as well, Kristy splits her time between Portland and Mt. Hood. Her work as an Airbnb Ambassador will help garner ongoing support for our organization as we continue to grow and develop.

Long-time leader and 2023 Board of Directors President, Dabney Tompkins is wrapping up his leadership role with the organization and will be handing over the reins to a new president to be elected by Board Members in December. His contributions have been vital to the success of the organization and his efforts will surely be missed. We're lucky to retain his bookkeeping skills to keep our ledgers tidy, so he'll definitely still be involved. Thank you for your contributions as a founding member and Board Member for the past six years, Dabney.

Likewise, Ryan Tigner with iTrip will be exiting the Board of Directors after serving several consecutive terms. He'll remain involved in Host2Host and will continue to serve on the Travel Portland Board of Directors. Thanks, Ryan, for your guidance and contributions over the years.


Lastly, Host2Host founder, Debi Hertert is stepping down from her role as Education Committee Chair. Her positive energy, enthusiasm, and people-wrangling skills are going to be very missed in this position but we are happy that she will remain a part of the committee and you'll still have the chance to connect with her at events. Thank you, Debi, for shining a bright light on Host2Host and coordinating spectacular events over the years.

If you are interested in volunteering for about an hour a month by joining one of our committees or even the Board of Directors, our organization could really use your help! Email info@host2host.org to get connected!

Tax time got you scratching your head? It can be pretty confusing to consider the federal, state, and local implications of renting your home or even a room on a short-term basis. 

Rental Income is Generally Taxable

First and foremost, the money you earn from renting out your home or room is typically considered taxable income. This means you should report this income on your annual tax return both state, federal, and even locally in some jurisdictions. 

Deductions can Offset Income

While you may have to report and pay taxes on your rental income, you also have the opportunity to deduct certain expenses related to the rental. Common deductions include:

• Cleaning and maintenance fees

• Utilities (only if included in the rental price)

• Advertising or listing fees

• Property insurance

• Depreciation of the rented space

• Other related expenses

It's crucial to keep detailed records of these expenses as the IRS might require proof if you get audited.

Considering your Primary Residence

If you rent out a portion of your primary residence, things can get a bit complicated when you decide to sell your home. Normally, the sale of your primary home can qualify for a tax exclusion ($250,000 for single filers and $500,000 for joint filers). However, if a part of your home was used as a rental, you might owe taxes on the gain attributed to the rented space.

Local Taxes & Regulations

Aside from federal and state income taxes, localities also impose occupancy and/or hotel taxes on short-term rentals. It's essential to check with your local city or county government to see what taxes or regulations apply.

Ignoring these could lead to legal trouble.

Conclusion

Renting out your home or room on a short-term basis can provide a welcome boost to your income. However, it’s essential to stay informed about the associated tax implications. To ensure you’re fully compliant and taking advantage of all possible deductions, consider joining our conversation on November 9th with local tax experts. It’s free for members with a small fee for non-members.

Written by Alan Colley, Host2Host Founding Member, former H2H President & co-host of the Summit Prairie Fire Lookout Tower in Tiller, OR

Each gathering around the table has its own dynamic. 

Coffee shared with another is infused with its own unique energy. 

Each and every interchange we have with a guest has its very own dance. 

The skilled host knows how to sing and dance so everyone wants to dance and sing along.

..................................
From an article in the Summer 2022 issue of Orion magazine...

“Ultimately, a society’s laws and policies change because the hearts and values of people change. And art, in all its forms, provides a direct route to people’s hearts, regardless of culture or background….The [whatever] movement needs artists and writers of every stripe just as much as it needs lawyers, scientists and activists.” (Manish Bapna)

This quote prompted me to think more deeply about how much this sentiment could so easily apply to hosting. Yes, we need people who are skilled in the mechanics and logistics of how to run a hosting business, but we also need artists and poets who raise our imaginations about the grand possibilities of hospitality and welcoming.

I want to ponder…

The poetry of hosting.

The song of hospitality

The delightful dance of welcoming. 

Isn’t this what calls us?

Isn’t this is what draws us in

and gives us the energy and spirit that carries us along?

Isn’t this what our guests feel from the first encounter?

Perhaps we could explore this poetry as the current that reaches beneath our work and lifts us as both guests and hosts.

In October, we hosted yet another terrific meet-up to provide tips and tricks to help hosts survive the upcoming slow season. 100% of attendees agreed that they experience at least one lull during the year, with January and February identified as the slowest months.

Thanks to panelists Anthony Rallo (H2H Board Member), long-time host Lorell Miller, Amina Moreau (Radious Founder), and even me, Charity Kuahiwinui, Host2Host Executive Assistant, who provided lots of ideas to help boost winter sales and up-level your hosting game.

Debi Hertert, H2H founding member kept the conversation uplifting and impactful. There were also tons of meaningful contributions from attendees.

Suggestions included:

• Updating your title, photo descriptions and listing text - potentially AI-assisted

• Performing routine maintenance like mildew removal - Wet & Forget came highly recommended (paid link, could earn a commission)

• Jumping on the Airbnb-suggested discounts for open dates

• Staying in your property and exploring the surrounding area as a guest would

• Refreshing items in the listing that are broken or missing

• Signing up for guest communication automation software like Hospitable

• Identifying indoor activities to recommend to guests in off-weather seasons

• Consider taking new photos of the space after you've made significant changes. Time your professional photos for early spring to take advantage of the light and supporting foliage.

Hopefully this information sparks some ideas for you and that you are able to gain a little inspiration and a few ideas for how to improve your listing. Sign-up now for our next, informative meetup covering taxes for short-term rental hosts on November 9th.

An in-person event sponsored by Travel Portland and Airbnb On September 21, 2023, Host2Host was most fortunate to bring together an incredible collaboration of overwhelmingly positive, thoughtful contributors to the short-term rental market in the Portland area and beyond.  Expertly moderated by Host2Host President, Dabney Tompkins, panelists included: Jeff Miller, CEO & President of Travel Portland Megan Beyer, Senior Policy Advisor for City Commissioner Carmen Rubio Justin Lindley, City Planner from the Bureau of Development Services Jordan Mitchell, Public Policy Advisor for Airbnb Also present for audience questions were experts in their field like: Alex Bland, Regional Advocacy Manager for Airbnb Kate Baumgartner, Public and External Affairs Strategist from Travel Oregon Scott Karter, CPA, Audit and Accounting Manager from the Department of Revenue Each of the panelists presented their perspectives about the state of the short-term rental market and shared as much information as possible about insights they’d garnered on the industry providing quality content for hosts in attendance. Sponsored financially by Travel Portland with drinks provided by Airbnb, it was a fun reason to gather together and learn more about some of the recent changes to permits in Portland and the implications this has for hosts. To learn more, members can review the slideshows presented by our panelists: Travel Portland, Airbnb, and Host2Host. Additionally, we were excited to having the opportunity to highlight a brief video submitted by Host2Host supporter, Fabstayz but unfortunately experienced technical difficulties. Be sure to check it out here! Once formal presentations were complete, the audience was given the opportunity to gain valuable insights by submitting written questions in advance to receive direct answers from panelists. Following the Q&A portion of the program, attendees were invited to meet and mingle panelists and subject matter experts as they enjoyed delicious craft beer supplied by Oregon Public House. At this munificent event, new faces as well as old gathered in a convivial and harmonious way to celebrate one another, learn insights about our shared interests, and support no less than six non-profit organizations: Host2Host, Oregon Public House, and their four designated, local non-profits. It was a WIN-WIN-WIN! If you're not a member and want to join, registration fees paid for this event will be refunded as long as you join by September 30th, so sign-up today!

On September 13th, we were joined by Minut Partnerships Manager, Alondra Palomino to talk about practical and technological ways hosts can protect their properties from risky reservations. She also offered an awesome discount for Host2Host members. You can access that information on our Members Only Video resources page.

Common Myths and Facts about Hosting
Before jumping into the presentation, she took a minute to dispel common myths about the short-term rental industry. One myth that was surprising was that most short-term rentals suffer from noise issues, but the reality is that only 40% have a problem in a given month. Unfortunately, this number is still high and can impact neighbor relations. 

Did you know that overwhelmingly, most guests seek out sustainable properties and spend 40% of their overall trip expenditures in the neighborhoods where they are staying? Make friends with the local businesses near your rental and make sure they know this statistic too. Maybe there are simple ways you can increase guest visits to their small business.

Take a Practical Approach
Next, Alondra provided super practical guidance to help hosts avoid introducing a risky reservation into their rental. Before a guest arrives, take a look at their profile and ask questions about their trip that can improve the guest experience and your own hosting liabilities. Consider tools that can help screen guests like those offered by Proper Insurance and safety courses offered by Breezeway.

Take a hard look at your house manual. Does it include all the basics like maximum number of guests, parking, quiet hours, and security deposit details? Is it a physical copy or digital as is offered by Touchstay or Hostfully? To help those guests seeking sustainability, it should also include information about recycling and recommendations for local businesses in the neighborhood. 

How Tools Can Protect Hosts and Property
Finally, Alondra spent a little time introducing tools from Minut that can help hosts be vigilant about the happenings in their rentals without being intrusive to guests. Minut offers a wide variety of tools to help hosts that can be turned off or on with every new arrival. Some of these include noise monitoring, occupancy monitoring, smoke alarm monitoring, termperature detection, mold monitoring, and even cigarette smoke detection. With indoor and outdoor monitoring solutions, Minut has you covered. Their easy-to-use app keeps hosts informed without being intrusive or overtly conspicuous to guests. Make sure you’re being a good neighbor and consider a tool like Minut for your hosting toolbox.

Written by Alan Colley, Host2Host Founding Member, former President & co-host of the Summit Prairie Fire Lookout Tower in Tiller, OR

Over the years of our work in the welcoming business we find a common theme among the entries our guests have written in the journal we have for them: Coming here feels like coming home.

Different folks put it differently, of course. 

Talia wrote, “As someone who hasn’t had much of a home or a family most of their life, being able to come here and get to know the two of you has felt like a refuge, a return, and a beginning all at once.”

David mused, “Anyone can put a house up in the air, but not everyone can make it a home. That’s what you have done - made one sacred place a home for countless strangers. Strangers who now call you both friends.”

The Power of Home

For many it seems that this place has surprised them, calling it magical, and opening them up to possibilities hidden or newly discovered in their lives. 

Isn’t that what home can be? A belonging so sure and safe that the whole, wide world opens up. 

In a world usually so fraught with fear,  disconnection and displacement, yearning for the peace and power of home may be the best gift we have to give.

Welcome, Strangers

I suppose many who read this may be tempted to dismiss my ramblings as frivolous to the serious work of hosting. That is their privilege, naturally.

I am inspired to think and write as I do about these ideas of home and belonging by a statement made by Chip Conley when he was being interviewed to become head of global hospitality for Airbnb. He said that the best way to measure the success of Airbnb would be when they were nominated for a Nobel Peace Prize. 

Whether you agree that Airbnb, or any booking platform for that matter, lives up to that ideal, for me it shifted everything about why we host and continue to welcome strangers into our homes. This is where I want to live, with the idea in my heart that each person we welcome into our home serves to dissolve the separation and alienation we see so prevalent in our world.

My question for you, fellow hosts ...

Isn’t this a concept worth our embrace and pursuit as we offer the gift of our homes to strangers?

Written by Host2Host Executive Assistant, Charity Kuahiwinui, former co-host in North Portland and co-founder of Ensourced

I moved to the Big Island of Hawai’i at just 18 years old. I was new to the world, but old enough to experience the true meaning of `ohana. My (now) wife’s family took me in and, with few exceptions, made me feel like I belonged, like I was a part of something larger than myself. They taught me the true meaning of aloha and as trite as this Disney soundbite may be, that “`Ohana means family and family means that nobody gets left behind or forgotten.”

It wasn’t always or even often sunshine and surf life for us. We managed to scrape together enough for a studio apartment in the worst part of Hilo and drove 1.5 hours one-way through windy roads up mountains and around horseshoe turns to work at five-star resorts on the other side of the island. This was our first exposure to the hospitality industry. We worked hard, often pulling double shifts, hitchhiking to work when the car was broken, and sleeping on the beach to save gas. 

Non-Profit Experience Runs Deep

Eventually, we made the leap to the smaller but more commercially viable island of O`ahu for better job opportunities. It was there I began working in administrative roles for now-defunct bookstores, law firms, and eventually a non-profit - the esteemed, Ronald McDonald House Charities of Hawai`i. Because of the general lack of quality healthcare options on nearby and far-flung islands, we cared for families during the most difficult times of their lives - from neonatal urgent care to pediatric cancer treatment, attending funerals and mourning together. The work was emotionally tough but rewarding, and the children always managed to make you smile. While there, I had the opportunity to travel to Maui to assist with a fundraising event. 

Our First Real Vacation

My wife, Maylene, joined me, and we took a few extra days over the weekend to tour the island and have a mini-vacation (our first). We woke up in the wee hours of the morn to catch sunrise on Mt. Haleakala. We drove our rental car exactly where the official agency maps told us not to but where the local shuttle bus driver said it would be fun – over dirt roads through up-country, around the eastern part of the island, then onto windy Hana Road. Later that day, we had the most terrifying drive of our young lives when we drove from Kahului to Ka`anapali on the one-lane road with two-way traffic, blind turns, a steep mountain on the left, and sheer cliffs with no guard rails on the right. I’ll never forget how we had to honk around every blind corner to make sure the way was clear and the time Maylene had to reverse up the steep road because a line of locals was coming the other way. We paused at that turnout, studying the crashing waves hundreds of feet below, caught our breath, and steadied our nerves before continuing onto Lahaina town. 

Arriving in Paradise

When we got there, it felt like an absolute paradise after that harrowing experience. Peaceful and serene - with much of the town preserved from whaling days in the late 1800s and as the former capital of the Kingdom of Hawai`i, history was all around us. We cooled ourselves under the nourishing banyan tree and took in the sites and sounds of the city. Barely old enough to drink, we greedily guzzled every last drop of that very special place. Maybe you have too.

Everything Changed in an Instant

That’s why our hearts ache for the fire that recently struck Lahaina and engulfed it in the worst possible way, roaring through paradise, and resulting in utter destruction. Livelihoods were lost. Homes were lost. Pets were lost. Lives were lost. 

The extent of the damage will not be known for some time, and we are left wondering how the area will ever begin to recover from the damage, intrinsically understanding it will never be the same.

So, while you can, hug your loved ones (even if virtually) and tell your `ohana just how much they mean to you. Tomorrow is not promised. 

Be Responsible Hosts with Guest Safety at Heart

Then, think about how you can help keep your guests safe in the case of an emergent situation. Do you have adequate carbon monoxide, smoke, and fire detectors? Do you test them regularly? Each bi-annual time change provides a memorable testing cycle so you don’t forget.

Do you provide fire escape ladders for multi-story buildings? How about fire extinguishers or even fire blankets that are easier to use in the kitchen?

Do you provide emergency evacuation information and phone numbers for guests? International visitors might not have that information readily at hand.

Do you have ways to communicate with your guests when urgent situations arise? The plans you put into place now, when you’re not faced with an emergency can truly save lives when one is happening.

Send Your Aloha to Maui

And, if you’d like to help the good people of Maui, consider a monetary donation to one of these reputable organizations:

• Hawaii Community Foundation, Maui Strong Fund
• Lahui Foundation, Fire Recovery Efforts
• Hawaiian Council, Kākoʻo Maui
• UH Foundation, Help Maui

Written by Alan Colley, Host2Host Founding Member, former President & co-host of the Summit Prairie Fire Lookout Tower in Tiller, OR

Oh my gosh! Hosting is messy!

No matter how much we plan and scheme to provide warm welcome, a wild card is bound to show up. Each guest, the one we know and the new ones we are meeting for the first time, show up with all the stories of their lives coming along with them.

No matter how much we prepare, we simply have little clue as to how they will experience us and our spaces in this moment.

Would we want it any other way? Isn’t the excitement our getting to greet and to get to know this wide spectrum of humanity we have offered to welcome to our doors? Of course it can be intimidating on some level. I totally understand this! But if we are serious, this is part of the reason we have decided to be a host in the first place - to expand our sense of hospitality, to open our hearts to the wider humanity.

I advocate that we recognize our guests as potential friends who may enrich our lives. I am advocating that we dial down our fears and suspicions enough to see the wonder of others, and, yes, to admit that no matter how much we want to nail down the perfect place and experience, hosting is a messy conversation that just might be worth celebrating. Thank you for being a host!