Updated on May 7, 2023

Residents of Oregon’s largest city take pride in their identity as trailblazers. It’s evident in everything from the name of the city’s professional basketball team, the Portland Trailblazers, to a milestone ordinance in 2014 that made Portland the first city in the nation to legalize short-term rentals.

Portland has continued to blaze trails in the short-term rental industry.

In February 2018, Portlanders Debi and Rob Hertert founded a trade association for short-term rental hosts. Known as Host2Host, the nonprofit organization now provides advocacy, community, and education for over 2,000 community members, including paid members, businesses, and Facebook groups. The group provides “a voice for Portland short-term rental hosts without corporate interests attached,” Rob Hertert said.

Rob and Debi Hertert, founder of Host2Host for Portland short-term rental hosts
Rob and Debi Hertert

Not long after organizing, Host2Host’s well-coordinated and passionate advocacy in the face of a proposed change to the city’s short-term rental ordinance helped to secure for Portland short-term rental hosts representation on the board of Travel Portland.

In doing so, Portland may have set another national precedent: Travel Portland designated two board seats to the short-term rental industry – one to a vacation rental platform, Vacasa, and another to a short-term rental host from the community, Shannon Hiller-Webb, a Portland home-sharing host and business consultant.

Travel Portland President Jeff Miller said as far as he knows, Travel Portland is the only destination marketing and management organization (DMMO) with board seats designated specifically for the short-term rental hosts.

As the city’s tourism promoter, Travel Portland is largely funded by lodging tax revenue to which short-term rental hosts contribute.

Speaking up for Portland short-term rental hosts

The proposed ordinance imposed a 2% Tourism Improvement District (TID) fee on hosts who use vacation rental booking platforms to accept reservations and a $4-per-night Transient Lodging Occupancy fee on reservations made through booking platforms and transient lodging intermediaries. (The TID fee went up to 3% last March.)

Host2Host members said they noticed that hosts’ voices were missing at the table when considering these taxes and fees.

Vacation rental platforms have their own interests that don’t always align with hosts, Shannon said. Moreover, hosts live in the city and are constituents. Many hosts rent out rooms in their home so they can age in place, according to a Host2Host survey. 

With details of the proposed change coming relatively last-minute, Host2Host had only five days to rally and organize their members to speak to city council before an initial vote took place on June 13, 2018.

Host2Host didn’t oppose paying the 2% Tourism Improvement District fee. However, they wanted the fee to be applied fairly by removing a provision that exempt hotels with 50 rooms or fewer.

Hosts also argued that the flat fee of $4 per night on reservations, regardless of the size or price of the room, disproportionately hurt low-income hosts and guests. Instead, they advocated for charging a percentage of the nightly rate as a fairer option.

Orchestrating a unified message to Portland city council

Host2Host quickly organized to identify hosts who could speak at the council meeting and dig up facts to support their arguments.

Fifteen hosts gave testimony to the city council and Host2Host members who attended the meeting wore yellow ribbons to identify themselves.

Shannon crafted testimony with a connected storyline for all 15 speakers. Their testimony accompanied an integrated PowerPoint presentation to visually and orally share with city council how short-term rentals positively impact the city. The testimony highlighted how hosts serve as ambassadors for the city by guiding guests to small, local businesses within Portland’s 95 neighborhoods.

Hosts asked the city council for recognition as a vested party and a greater voice in the decision-making process for regulations and tourism promotion.

After all, many of the 8.8 million overnight stays in the Portland area each year are at short-term rentals. Those visitors spend about $5.6 million and generate about $277.8 million in tax and fee revenue per year, according to the most recent numbers from Travel Portland.

About $13.8 million of that $277.8 million in revenue came from short-term rental taxes and overnight fees collected by the city.

Earning a seat at the table of tourism promotion

At the time of the meeting, Travel Portland had already planned to fill one of the board’s 28 seats with a representative from a short-term rental platform but had not considered a host representative.

Even before Host2Host’s presentation was over, Portland Commissioner Amanda Fritz took the mic to say that she believed that hosts deserved representation on the Travel Portland Board of Directors.

Her comments drew an eruption of applause from short-term rental hosts.

Debi said she felt the presentation was well-received because “it showed professionalism, organization, and continuity, as well as the obvious passion and support of the host community.”

Shannon Hiller-Webb

Over the coming months, Travel Portland reached out to Host2Host for a list of nominees to the board seat. After conducting interviews, Travel Portland selected Shannon to represent hosts on the board. She participated in her first Travel Portland board meeting on Jan. 28, 2019.

Representation on the board was a huge step forward for Portland hosts.

“Initially, I think all of us viewed it as a massive win for the voiceless. We’d been voiceless for so long,” Shannon said.

However, hosts still had very little influence compared with hotels. Fifteen out of 28 seats on the board go to hoteliers, and just two seats go to the short-term rental industry. Meanwhile, the representative for the short-term rental platforms, Vacasa, did not regularly attend meetings, Shannon said.

“I was the lonely person in the room representing our industry,” she said.

“Sitting at the table, I would listen to our industry vilified in front of me. Hoteliers would say, how do we be more competitive against short-term rentals? How do we legally approach getting them out?”

Building relationships with decision-makers

Behind the scenes, Shannon built relationships with the Travel Portland executive team.

“I was trying to impress upon people our work in the community and our knowledge of the community and how that could impact their decisions and impact and inform their influence,” she said.

The Covid-19 pandemic brought home many of Shannon’s points on how short-term rentals contribute to Portland.

“For the first time, short-term rentals outpaced hotels for the highest nightly rate because in the era of Covid, you could do a full house booking with a sense of safety they weren’t getting with hotels,” Shannon said, “so I think we’ve become a stronger component and gained some respect that we are a valuable contributor to [Travel Portland] financially and need to be recognized and supported equally.”

In late 2020, Travel Portland and Airbnb partnered on a $25,000 marketing campaign called “Rediscover Portland” to promote the city in the wake of Covid and riots which had slowed down tourism.

Travel Portland coordinated with Host2Host to help identify the neighborhoods to highlight in the campaign.

“One of the things that Travel Portland was doing early on in my relationship with them was making decisions without informing us or involving us. If I’ve had any wins, it’s that I’m now getting them to call us in advance and talk to us and say, hey, this is something we’re planning, and do you have any thoughts?”

City officials also now seek feedback from Host2Host on proposed changes to regulations.

“They ask us to give expert testimony if there are court issues, and they are directing hosts to us who have questions they cannot answer,” Debi said. “In addition, they are willing to do presentations to our groups when there are issues that hosts benefit from understanding.

“We have a respected place in the government offices, and Host2Host is recognized as the voice of the hosting community.”

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