Crystal’s ‘Trapper Keeper’ & Rent Well: an innovative beacon for technically homeless struggling to avoid the streets

Poor for a Minute
Open: Housing
Published in
10 min readFeb 19, 2017

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You could tell how seriously Crystal O’Connor was taking Joan Mershon’s Rent Well class on a recent Saturday just by looking at her three-ring binder. Impeccably organized, layered with color-colored Post-It notes, it was every bit the 2017 equivalent of a Trapper Keeper.

“When my whole life is out of control, at least I can control what’s in this binder,” she said.

O’Connor, 39, used to have a real Trapper-Keeper growing up in Portland in the 1980s. Since then, her life has taken a few twists and turns, and her embrace of organization now is about getting back into an apartment — the step officials have told her is required to bring her son home from “juvy.”

O’Connor is homeless, among the thousands of metro-area families and individuals who meet HUD’s definition of “homeless,” but are “doubled up” or “couch surfing,” not on the street and in the public eye. In O’Connor’s case, she’s currently crashing at her cousin’s with two children, while the teenage son languishes in juvenile detention.

Crystal O’Connor. Photo courtesy of O’Connor.

It’s not clear what the current numbers for this homeless-but-still-sheltered group are in Portland — the category was estimated at 12,000 two years ago during the 2015 biannual Point-in-Time count, more than three times the 3,800 on the streets at that time. A new count conducted last month may soon give a clearer picture. However, given Portland’s continuing red-hot housing market forces and steady news of huge rent increases, the number could be a lot higher in 2017.

A year ago, O’Connor says, her husband left her and her three kids with only her minimum wage cashier’s income ($1,400 gross per month, she says) to pay $1,350 a month rent for a three-bedroom apartment at Hamilton Park Apartments near SE 122nd and Division. Amazingly, for months, she scraped by while paying a hundred percent of her income on housing, using her tax return to hang onto the family’s “home base.”

With 100 percent of income going to housing, though, moving out was only a matter of time. The straw that broke the camel’s back, she says, was an already-approved, signed $500 rent assistance check that county workers never mailed. During a two-week period around Christmas, the family was on the streets, and O’Connor’s teenage son made a poor decision that landed him behind bars. (She declined to discuss specifics or share his name.)

“I was supposed to get $500 from the county, but they never mailed it,” O’Connor says. “It was to help with the remainder of my rent, but they forgot. I called and called and called, and finally somebody got back to me and they said ‘well we just found [the check], we forgot to put it in the mail.’”

“I said, ‘Well, it’s too late, I’m getting evicted.’”

Eviction is far from the only barrier O’Connor’s faced. She’s gone to counseling in the past to cope with anxiety and post-traumatic stress, she says, but “right now I really don’t have the time.”

Also: it never helps when your therapist can’t stay awake.

“The last therapist I saw fell asleep during both our sessions, so I haven’t been back since,” she said.

Are you &*@#$! kidding?

“It’s awful,” O’Connor responds, a melodious laugh sparkling through the cellular signal, suggesting a sense of humor is a key to her continuing resilience. “I was like, I’m better off talking to my friends. They don’t fall asleep when I’m talking to them, they care about me, they’re listening to my thing, they’re not dozing off, pen falling out of their hands.”

O’Connor’s eviction came a few months before the Portland City Council passed a new ordinance requiring landlords to pay moving costs for tenants — an ordinance O’Connor’s Rent Well teacher, Joan Mershon, discussed at length with her students. (The ordinance covers tenants who move due to “no cause” evictions or steep rent hikes, and would not have applied to O’Connor, who was evicted for nonpayment of rent.)

O’Connor says she had to get a storage unit, struggled to pay for transportation costs and “lost a bunch of my stuff because I couldn’t take it with me, and [the landlord] fined me for leaving it there.”

Finding Mershon’s class has been an eye-opener for O’Connor, she says: like many individuals experiencing homelessness and poverty, O’Connor was never taught some of the basics of how to, uh … rent … well.

How has Rent Well been for you so far, Crystal O’Connor?

“Really informative. I learned a lot of things about my credit, background checks, my responsibilities as a renter, also what is and isn’t okay when it comes to landlords,” she says. “In the past I’ve had things happen that didn’t make any sense because I didn’t know anything about it.”

“I think people need to know, the housing crisis isn’t just affecting people living in tents on the street, it’s affecting other aspects too,” O’Connor says. “It’s affecting our youth too, when they become homeless. There needs to be more help for people who are really trying.”

It’s a time of major growth and change for Rent Well, an innovative program which has flown under Portland media’s radar since its origins in 2009. Around that time, says current program administrator Caitlyn Kennedy, Rent Well separated from a similar program called “Ready to Rent,” which is still offered online at readytorent.org.

On July 1, Kennedy’s employer, Transition Projects Inc. took over a Portland Housing Bureau contract for Rent Well from longtime administrator Home Forward.

“I almost physically leaped over the table when I found out about this [job opportunity],” Kennedy says, laughing.

Why so inspired?

“Rent Well had been my favorite part of my job prior,” Kennedy says. “I was a housing specialist at a [domestic violence] shelter. I worked with all the individuals who were trying to get out of the shelter and get housed with no budget. Rent Well was a way people could start piecing together their own plans, start determining their own life and successes.”

Kennedy says it’s “a dream” to now run the program that helps people get their housing stability back. Like Ann Witte, the local tenant defense attorney we previously covered, Kennedy knows all too well how complex and daunting landlord-tenant and fair housing laws can be for would-be renters trying to overcome generational cycles of poverty.

“So many light bulbs happen constantly,” Kennedy says.

These days, Kennedy trains and certifies instructors in the greater metro area: Multnomah, Washington, Clackamas, Clark and Cowlitz Counties. The class is a 15-hour curriculum that offers a toolbox — hope — to renters with barriers.

The most common barriers for Rent Well students are landlord debt, poor credit, criminal history and evictions.

A request to create a statewide landlord guarantee fund — the necessary first step to offering the class across Oregon — is now in Governor Kate Brown’s budget, Kennedy says. A new-and-improved curriculum arrives in April, that Kennedy says will better integrate Washington State landlord-tenant laws, “beef up the credit part of it” and “look a lot fancier.” TPI is hoping the curriculum can be offered on a statewide (Oregon) level as “there have been a lot of requests from other counties” to offer it, Kennedy says.

Currently, the program is paid for by the Portland Housing Bureau, but the landlord guarantee fund is supported by local counties. The idea of the guarantee, and a certificate that goes with it, is that if a Rent Well graduate gets evicted, a landlord can be reimbursed for damages or unpaid costs. Currently, that guarantee amount is $2,000 in Multnomah County, $1,000 in Clark County and “between $700 and $1,000” in Clackamas County, Kennedy says. “Washington County, unfortunately, lost their guarantee fund,” she adds.

Since July, when TPI took over, 239 have graduated RentWell in Multnomah County alone, Kennedy says.

The guarantee can be a crucial extra layer of protection and incentive for landlords to open their doors to a prospective tenant whose rental history or background check raises red flags.

Even as hundreds of families have used the program to get back into housing since its first days, the data shows the guarantee fund has barely dented public coffers:

Of the 239 who’ve graduated Rent Well since TPI took over, Kennedy says, “only 11 currently have registered with a landlord to possibly use the landlord guarantee in the future.” Typically, the percentage of those landlords who end up actually requesting reimbursement — for example, due to damages above and beyond the amount of the deposit — are only a small fraction of that number.

Only 6.5 percent of graduates used the landlord guarantee fund from 2009 to 2016, Home Forward data shows, and less than 1 percent ever requested a claim.

58 percent of Rent Well graduates were homeless at the time of their graduation, Home Forward data shows. The self-identified rental barriers for participants during that 2009 to 2016, pre-TPI phase were:

  • No money for moving 58%
  • Eviction 45%
  • Landlord debt 42%
  • Criminal history 38%
  • Credit problems 36%
  • Bad reference 27%
  • Substance abuse 19%
  • No rental history 13%

Joan Mershon, a former TPI employee whose small business is called LifeAbility, has been teaching Rent Well since its early days, in 2009. In between sips of Diet A&W and offering up chocolate espresso beans, Mershon tells it like it is, with contagious energy.

The local wifi signals are named “GetTheMostOutofLife” and “LifeisGood.”

As Mershon, in bob and glasses, khakis and knit shirt, gives participants a handout about the new city ordinance offering reimbursement of moving costs, she doesn’t mince words, or equivocate about the potential pitfalls of renting for poor people. The class is the housing equivalent of a “come to Jesus” moment, bringing to mind the feeling of a Bible study group, Alcoholics Anonymous meeting, or continuing ed class.

“I don’t want anybody to sugarcoat anything,” Mershon sternly tells her students. “You don’t do anybody any favors when you sugarcoat.”

“There’s a lot of things that are not clear [about the new Relocation Assistance Emergency Ordinance],” Mershon says, passing out a factsheet.

There are a lot of rumors out there about it, a participant says.

“That’s why I got this sheet for you,” Mershon says. “This sheet is not rumors.”

When one participant complains about a certain landlord, first name Oskar, who Mershon calls “a poster boy for slumlords,” she shares a few colorful anecdotes about Oskar’s past violations of fair housing law.

“That is a federal civil rights violation,” she says, when the participant notes that Oskar nearly doubled the move-in costs upon learning that he has help from an agency. She then instructs the participant to call the Fair Housing Council of Oregon.

Ultimately, though, she throws the question of whether to rent from him back to the questioner: “It’s a personal choice you got to make — is this worth it?”

This, in a nutshell, is Rent Well: the moment when a participant realizes they have a choice. Can have a choice.

They aren’t trapped like a rat in a cage.

“Let’s move on to something a little more cheerful,” she announces a little later, to groans and chuckles. “I want to talk about background checks.”

Participants are typically unable to see what landlords see via screening companies who perform background checks, Mershon notes. “You cannot just go get your own” background check, she notes. However, Mershon “gets to use the landlord door,” she notes, and obtain background reports for participants.

This is the kind of helping hand that can make all the difference for participants like Crystal O’Connor.

And if the participants didn’t have enough motivation when they signed up for the class, there’s a poignant reminder right around the corner, of an even rougher reality waiting for them if they can’t regain control of their housing situation.

That would be Washington High School, the location that a year ago was to be the site of a now-cancelled “navigation center” for homeless, currently the camping spot for at least a dozen unsheltered homeless people.

Crystal O’Connor. Photo courtesy O’Connor.

In Mershon’s class, on the same day this writer visited, O’Connor learns her landlord debt is almost certainly over the $2,000 limit held by even the most forgiving of landlords.

It’s a tough moment for her, but also a crucial step in her journey to retaking control of her life. She has some support systems, but feels like the safety net isn’t there for her.

“I can’t get that much help because I work, and I have a job, and I’m not addicted, and I’m not in a shelter,” she says. “I just need to get into somewhere.”

O’Connor knows that once she makes a payment plan, and gets back into a place, her struggles won’t magically, suddenly, be over.

“I don’t expect a huge change as far as financially, I know I’m still going to stumble. But it’ll make a change for my son, that’s the most important thing for me right now. It’s tough for him to be [in juvenile detention] and it’s tough for me to know he’s there.”

Her “Trapper Keeper” binder, and the newly organized, prepared Crystal O’Connor is her best resource for whatever comes next.

“It really paid off [in court] yesterday,” she said. “I was complemented on how organized I was, that I had notes written down, and was prepared to answer almost any question.”

“My son’s therapist was sitting next to me and he was like , ‘Wow, you’re so organized.’”

Why talk about her struggles publicly?

“I need to tell people my story, and my son’s story,” she says. “I can’t stop. I have three people who depend on me, and I will not give up. That’s what’s driving me every day.”

Know someone struggling with barriers to renting? Send them to Rent Well. Want to contribute to keep Rent Well afloat? Go here. You can send story ideas to, or contribute to Poor for a Minute’s survival using Paypal and this email: poorforaminute@gmail.com.

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We are all poor due to the broken social safety net in the United States, the world’s richest nation. Portfolio, bio, contact: ThacherSchmid.com