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We’d been looking for something modest, a nice loft, or a cute little one-bedroom in Portland, Maine, where I’d been teaching yoga for about a year, even before the pandemic hit. We ended up instead with a 4,000-square-foot, three-family home—way beyond our budget. This speaks both to the wilding market in this city, and around the country, and to our mid-COVID headspace. The whole world felt crazy and uncertain, but also like the walls were caving in. Sure, I thought. Why not this?
We got pre-approved with zero trouble (which does not mean actually getting the mortgage came easy) and put in an offer a little over asking. I wrote a very good buyer’s letter I was later told helped push us to the top. After the sale went through, my lawyer-father—who’d until then kept his mouth shut—wrote to tell me that I didn’t have the disposition to be a landlord. “Your tolerance for bad behavior is limited,” he typed. “You will be offended that someone doesn’t treat your property the same way you would. They won’t. You’ll have tenants and guests that will leave the place a mess, steal or break things, annoy your other tenants, bring pets (even though you may prohibit it), try to scam you, complain to housing authorities, and give you bad reviews.” Hmm, I thought. I guess that’s why not?
The house, in Portland’s industrial-residential East Bayside neighborhood, had been built in 1900 and completely renovated in 2017 with the specific intent of using the first and second floor units as income-generating, short-term rentals; the third was set aside for the then-homeowner and her daughter. Led by Portland architect Leslie Benson, dark and stuffy rooms were transformed to bright, open layouts. To meet a fairly modest budget, Leslie worked with the existing structure and window locations and didn’t touch the tiled exterior (aside from a dramatic navy blue paint job), the dusty driveway, or the dodgy carport out back. The most work—and the most money—was put into the top floor unit. It was taken down to its studs, reconfigured to maximize light and offer water and sunset views from the kitchen, and leveled to eliminate what Leslie calls “vertigo inducing slopes.”
We bought the house completely furnished (I know), and three days after closing I had tenants in both units—a friend and her son in one and three college kids on leave from school in the other. The college kids worried me, but I liked what they were doing here (working on a Democratic election campaign), as well as the idea of filling the space so quickly. Plus, one of their fathers paid for the entire three months up front.
That was a year ago. To be honest, the biggest challenge I’ve had as a landlord and Airbnb host has been managing my own anxiety about having the apartments open for too long—a general where’s-the-next-check-coming-from panic that’s familiar from having spent 13 years as a freelance writer. In between longer-term tenants, I’d make the apartments available for short-term guests—ideally keeping one apartment filled with a steadier tenant and leaving the other open for the more lucrative quick stays. I created profiles, listed the apartments on several sites, and kept steady watch of my calendars, worrying equally about double booking and not booking at all, until I realized it was much less stressful to just pick one listing site. I’ve found Airbnb the easiest to understand, manage, and (when needed) get support from.
Finding help, of course, has been essential. So has buying in bulk. In my first few months of short-term renting, I did a lot of frantic laundry in between guests, until I decided to give myself a break and just spring for more sets of sheets and towels. I’ve slowly collected a small team of cleaners and turnover staff, mostly mined from my yoga studio. But I’m still doing the managing, which means if a hairy drain needs to be snaked or the toilet paper holder comes off the wall, I’m the girl to do it, and, of course, Murphy’s Law means that sort of thing only happens when I’m several hours away.
This summer, a few long overdue projects—siding repair, a new driveway—were all last-minute scheduled for the same time, coinciding with some jackhammer-heavy street work that started every morning at precisely 7 a.m. I gave lots of partial refunds—not because anyone asked, and at least as far as the street work goes I can’t guarantee people peace and quiet in a city, but because it’s important to me that they enjoy their stay. Also because I am now a slave to reviews.
Aside from some art books and a cute marquee sign that read “Welcome to PWM” that went missing pretty soon after I started welcoming short-term guests, my father’s predictions have not yet come true. There have, of course, been small—though still annoying—issues, like trash mixed in with the recycling or tenants in my parking spot. Sometimes I suspected people were smoking pot in the house—a violation of the lease because I’m terrified of a house fire not to mention smoke-infused walls—but bringing it up resulted in a corner of the carport becoming a little outdoor smoking den, which didn’t feel much better. (Oh, and I might not rent to a friend again—we’re still friends, but it could have easily gone the other way.)
But for the most part, everyone who’s come through this house has been respectful, friendly, and really glad to be here—which could have a lot to do with the sorts of people attracted to the city itself. Portland is really nice. And beyond the financial advantages, there’s been some solid satisfaction in learning how to not only fix a few things here and there, but also to stand up for myself, whether that’s with driveway pavers who don’t show up when they say they will or snow removal companies who drop your account mid-season (true, horrible story). And, of course, there is satisfaction in learning to be a great host. So far, at least, I’ve been able to keep people warm, safe, and happy, whether they’re here for a while or just for a weekend. And if you don’t believe me, you know how I’d suggest you fix that: Come visit!
