What if everything you own is for rent?

Two weeks ago, when I was gathering some friends around my dining room table in Portland, Oregon, my phone lit up. It was an inquiry on travel booking platform Airbnb, from a weary visitor looking for a place to stay after the host of the house you booked suddenly canceled. Was I available?

Sure, I wrote again. But it was 9pm, and I still needed to pack up for a nine-day trip on the John Day River in Oregon the next day. Can you wait an hour? I asked.

To my relief, I found another place to stay. Had she booked my two-bedroom bungalow, I would have sent my guests home and ran from room to room to grab clothes, food, and gear, put them in the car, quickly clean the house and find a place to sleep that night. In seven years of renting my house on Airbnb, it would have made a record, a request that came within five hours after, after Check-in time is 4 pm. But my life is for rent. I try to be ready for anything.

The way of life that boggles the minds of my friends began with some urgency. I quit my last full-time job in journalism a few years agoAnd the I had a little cash and a looming mortgage payment about to drain half of my meager savings. The summer had just begun, and I had little interest in the exhausting search for a new job in a struggling industry. But I needed quick cash, and Airbnb was my lifeline.

I arranged, took some pictures of the Northeast Portland home I bought just a year ago, created the listing and broadcast my living room to the world. At the height of Oregon’s golden summer, reservations have begun. In a few days, it will be my new home for someone else, and someone else after that, until Labor Day. I tossed some camping gear in a car and a kayak on the roof and the Beaver State Explorer set off on her prime.

My dining room, announced to the world on Airbnb.

Winston Ross

When I didn’t need to be in Portland, I set up home camps along the rivers I love: The Deschutes, McKenzie, and Klickitat. When I had an appointment with a dentist or doctor in town, I would find a new getaway, paddle along the Sandy or Clackamas riverbeds and set up a quick camp on a wild bank, half an hour from downtown Portland. In a month, my bank balance doubled. I was hooked.

Seven years later, I’m an Airbnb Superhost host, custom van owner and Subaru Outback pulling a teardrop-shaped trailer, all rented on three different platforms, all trapping me in the velvet coffin of a lifestyle that makes finding another full-time job hard to fathom. In some ways, it’s a twist on Vanlife, the movement promoted by millennials who priced out of the housing market, choosing to wait until the false promise of the American Dream and live as unattached nomads on four wheels. Unlike these vagabonds, my homelessness is the product of a growing participatory economic fleet, grounded in the same radical philosophy: that the promise of stability and sanity that once came with traditional professions, 401(k), and real estate purchases is a fickle one. One. In its place is the rustic but resilient culture of vanlife, in its many forms.

In the hills of Alabama, California, there is ample parking for pickup trucks, but the best spots tend to hijack quickly.

Winston Ross

Thanks to a wave of wildfire refugees and city people fleeing crowded big cities in 2020, this has been a remarkable year to be listed on Airbnb. I plowed the proceeds into a renovated kitchen, bathroom, basement studio, backyard deck and sauna, made from beautiful western red cedar shingles. Then, in search of a more stable housing option when the house was booked up, I found a Ram Promaster for sale and stuffed a queen-size mattress and some camping gear into it, and I explored Oregon that way all summer, absolutely ecstatic. The need to set up a tent. By the fall, I had enough proceeds to trick the truck, and I found a famous couple of full-time Insta vanlifers, Nate Cotton and Courtnie Hamel, who agreed to come live in my house for a month and turn the truck into a work of art, full of solar panels, radiant heat, Cedar wood cabinets and plush memory foam pillows that will transform from a bed to a sofa, in seconds. By the following spring, the truck was ready, and I skipped to sunny Arizona while Airbnb guests took over the house for two months, and fed my social cat so I didn’t have to.

When I returned, I met GoCamp founder, Deborah Kane, who urged me, impressed by Cotton and Hamel’s craftsmanship, to include the truck on the site. She said I can always block the calendar when I need it. I committed to this, and immediately the truck began accumulating reservations. I figured I’d be camping out when both the truck and the house were busy, but the 12-year-old hatchback sagged under a full load of equipment, and a nationwide rental car shortage was making headlines. So I bought Outback, and immediately included it on Turo. If all three were booked, I would make about $800 a day, more than enough for anything from a stay in a nice hotel in Portland to a last minute trip to Greece.

The Alsea the Border Collie makes a great truck companion, as long as she gets enough exercise during the day.

Winston Ross

What followed was a chaotic summer, as I worked through the kinks of running three hospitality companies while packing and unpacking wherever I was going. Most Airbnb guests are great. Sometimes it’s impossible, or they’ve learned that putting together a great enough list of “grievances” at check-in could earn them a refund. I once woke up in Iceland to a series of annoying messages from a guest who needed tech support for the entertainment center (unable to find the power button for the receiver) that I delivered from a hotel bed. I made angry complaints about a single tuft of dog hair, and dust on higher From the doorstep, a pipe in a hole at the end of my backyard. One female guest had a blind dog who she insisted was agitated as he smelled my cat, lying on the sofa outdoors.

Finding the perfect parking spot is one of Vanlife’s biggest challenges. This one, near Palm Springs, is at the end of a long, bumpy road.

Winston Ross

The truck rental business is no less stressful at times. The Promaster is a salvage (horrible decision, in hindsight) and required quite a few repairs in the two years since I bought it, with mechanical bills of over $1,000 after what felt like every booking, from the air conditioning to the sliding door sensor to coolant leakage bent on Stay leaked. A couple took her to a casino and left a dog inside while they were gambling. The dog smashed inside in a desperate attempt to escape. Someone else stopped her in downtown Seattle so they could stay in a hotel for a night, she was burgled right away, and everything could be easily removed by morning.

Renting an Outback promises to be even easier, because it’s brand new and it’s a car. Simple enough, right? But a Russian family called me over and over again during their eight-day trip, once because they couldn’t make a loud beep (the kids weren’t wearing seat belts) and another because they somehow disabled the alarm and couldn’t start the car. I didn’t even know the car had an alarm, let alone how to reset it.

Meticulous logistics, conservation ethics, and impeccable organizational skills are essential to this lifestyle of business. Fortunately, there is an entire industry of product and application companies that cater to our nomadic desires. This winter, I added hauling capacity to the truck with a nifty Front Runner roof rack system, and moved the bikes to a nifty Kuat hitch-mounted rack. SureCall signal booster increases my cellular charge and mobile hotspot coverage. Jackery’s solar panels keep Lion Energy’s power banks on top, so I never run out of juice when I’m camping off the grid, even if I’ve never plugged them into a wall. To find places to camp, I use iOverlander and Harvest Hosts, a great platform that connects wineries, distilleries, and breweries to travelers who might want to park a car on a vineyard while sipping on misty pines and IPAs.

When you work, the whole maneuver truly Works. This winter, I took another two-month trip to Southern California and Arizona, breaking up the rustic van left with a little splurge at three epic spa resorts: Canyon Ranch in Tucson, Castle Hot Springs north of Phoenix and Savannah, near Scottsdale. As a working journalist, I would never be able to justify riding snow into the desert to escape the worst of Oregon’s winter. As an entrepreneur in the sharing economy? you flush.

The occasional flaunting of luxury properties like Castle Hot Springs is a vital opportunity to recharge.

Winston Ross

When I got home, I signed up for Trusted Housesitters, a seamless platform that connects animal-loving travelers with hosts who need someone carefully screened to stay indoors and care for pets while traveling. My first session for two witch cats was in the Willamette Valley town of Philomath, a 40-minute drive from one of my favorite mountain biking trails. The day I started, I got an Airbnb reservation for two weeks. Sharing economic synergy at its best.

There are a lot of real costs to this method of separating from the matrix. Romantic relationships carry all kinds of turmoil. Some days are simply stressful, with belongings scattered scattered across my driveway or in my front yard sorting while I reorganize the next trip. It took a while for you to get used to the idea that my house wasn’t really my home. It’s more of a timeshare feature that I only stay in when no one wants it. I may have to give it up with a few hours’ notice.

An impromptu game of “park bowling” at a campground for truck workers near Joshua Tree. With a few amenities like a sun shower, kitchen and composting toilet, it has all the features a Bedouin needs.

Winston Ross

Still, as I write this, I nest in a gently swaying hammock, shaded by an already sweltering Oregon summer by a forest of crimson pines, and steps away from a cold stream, gurgling, duck liver pate and local goat cheese spread over rice crackers, planning your next kayaking trip On the Metolius River and then an evening buoy on the Deschutes in Bend, where I’ll be able to hear Bob Dylan croon from the platform at the nearby Hayden Homes Amphitheater. It’s not really a bad life.

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