Winning is as easy as 1-2-3! This year we're trying something different with an end of year Host2Host 1-2-3 50/50 raffle which gives you a chance to WIN BIG while supporting an organization that provides educational opportunities and advocates for YOU!

In this online raffle, 50% of the contributions will go to just ONE lucky winner and the remaining 50% will be contributed to Host2Host. That big winner could be YOU! 

To play, just buy your chance to win here and wait for the winner to be drawn at 11:30pm on December 31, 2023. Notifications will go out automatically to all contributors just before the bell drops on 12/31/23.

This is an online raffle, so invite a friend or two - you don't need to be a Host2Host member to play!

The charm of a short-term rental lies in its ability to provide a home away from home. With the holiday season upon us, many property owners are contemplating whether to add a festive touch to their rentals. This blog explores the pros and cons of decorating short-term rentals for the holidays, helping you decide what's best for your property.

Pros of Decorating for the Holidays

1. Enhanced Guest Experience:  Decorating your rental for the holidays can significantly elevate the guest experience. A well-adorned space not only looks inviting but also creates a festive atmosphere that can be quite appealing to guests seeking a special holiday getaway. This attention to detail often translates into glowing reviews and repeat bookings, making your investment worthwhile.
2. Marketing Appeal:  Holiday decorations can make your rental stand out in a crowded market. When potential guests are scrolling through dozens of listings, eye-catching holiday-themed decor can be the deciding factor. Professionally photographed rooms featuring tasteful decorations can enhance your listing's appeal, potentially increasing bookings during the holiday season.
3. Higher Rental Rates:  The holiday season often brings the opportunity to charge premium rates. A beautifully decorated space can justify a higher price point, as guests are willing to pay extra for a unique and festive experience. This factor can be important specifically for larger, whole house rentals in a vacation destination.

Cons of Decorating for the Holidays

1. Additional Costs:  Decorating a rental property involves additional costs, including purchasing, maintaining, and storing decorations. It’s important to consider whether the potential increase in bookings will offset these expenses. Opting for timeless and durable decorations can be a cost-effective strategy in the long run.
2. Risk of Damage or Theft:  With decorations come the added risks of damage and theft. Fragile ornaments or high-value items could be broken or go missing. Use decorations that are durable and not too expensive to replace and for goodness sake, no family heirlooms.
3. Diversity and Inclusivity Concerns:  Considering the cultural diversity of your guests is crucial. Not everyone celebrates the same holidays, so overly specific decorations might make some guests feel uncomfortable. A safer approach could be to opt for neutral, winter-themed decorations that celebrate the season without aligning with a specific holiday.

Best Practices for Decorating Short-Term Rentals

When decorating, aim for a balance between festive cheer and understated elegance. Safety should be a priority—avoid anything that could be a fire hazard. Also, consider storage solutions for your decorations in the off-season.

Decorating your short-term rental for the holidays can be both rewarding and challenging. Weighing the pros and cons in the context of your specific property and clientele is key. Ultimately, the decision should align with your business goals, your target audience, and the expectations of your guests.

An exciting new resource for visitors to Portland has recently opened in downtown’s vibrant West End: the Portland Visitor Center. A team of friendly, professional Portland experts are on-site to assist you and your guests — they can help plan a visit, answer questions, offer recommendations and so much more. Don’t forget to stock your rental with local maps and brochures from over 200 area attractions.

Located at 1132 SW Harvey Milk St., Suite 104 — just a few blocks from Powell’s City of Books and steps away from hotels, shopping, dining and attractions — the Portland Visitor Center is easily accessible. 

Amenities include cell phone chargers, a water-filling station, and complimentary Wi-Fi so it’s the perfect place to recharge your batteries. The center is an ADA-compliant, KultureCity-certified Sensory-Inclusive space, and there are even on-call translators and ASL interpreters available. 

It’s open Monday thru Saturday, 9a – 5p and Sunday, 10a – 3p. Can’t make it downtown? Visitors can call 503-427-1372 or 1-888-503-3291 (toll-free) to speak to a knowledgeable travel expert about whatever assistance they may need, whether they’re planning their next visit or if they’ve arrived in town. Either way, the good folks at Travel Portland’s Visitor Center are here to help!

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.