Crystal’s ‘Trapper Keeper’ & Rent Well’s beacon for technically homeless

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

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.

Read the full post on my blog about poverty in the Portland area: Poor for a Minute.