The Chicago Teachers’ Union and Affordable Housing: A Rant

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Happy October! The 2020 Chicago rental season is now over. The wintertime heating ordinance is now in effect. Now, tuck in with a nice cup of tea because I am about to go off about the Chicago Teacher’s Union and affordable housing.

“Trick or Treat!” We’re all going to be hearing it soon. Small children at the door asking for candy and chanting a phrase that has lost all significance over time. Originally it was a threat: “give us food or we’ll cause harm to your home.” Before that, “give us food to keep the evil spirits away, because this is the time of year when the barriers between our world and the afterlife are very thin.” Maybe the Chicago Teacher’s Union remembers the original meaning of “Trick or Treat.” They certainly are re-enacting it. “Agree to implement our plan for affordable housing citywide or we’ll strike, and hundreds of thousands of babysitters will be very, very happy for several weeks.”

With one week to go the CTU/City of Chicago employment contract negotiations have stalled over the teachers’ demands affordable housing, not only for them but for their students. You heard me. While the specific demands of the CTU have not been revealed, we can get an idea of the scope based on their website. I will include my interpretation of their demands below, with a few personal side notes in parentheses. Continue reading The Chicago Teachers’ Union and Affordable Housing: A Rant

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Kay Cleaves

Founder and owner of RentConfident. She's the primary developer of the website and research engine code. She's spent over 10 years working in the Chicago rental industry and has assisted with over 1200 leases.

A Day in the Life of a Landlord’s Leasing Agent

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I spent 10 years in the multifamily industry before starting RentConfident. For the first half of that time I was employed directly by the owner of roughly 50 Class C and Class D vintage walkup buildings scattered across the north side of Chicago. For the second half I was a licensed real estate agent focusing primarily on representing tenants in rental transactions across the city and suburbs of Chicago.

It has occurred to me that throughout the history of this blog I’ve spent a lot of time talking about what I learned during those years and in the time since I quit agency, but I haven’t really talked about what I did while I was working there. So for the next two weeks I’ll be doing “day in the life” articles, one from my time working for a landlord and the other from my time working for tenants. Continue reading A Day in the Life of a Landlord’s Leasing Agent

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Kay Cleaves

Founder and owner of RentConfident. She's the primary developer of the website and research engine code. She's spent over 10 years working in the Chicago rental industry and has assisted with over 1200 leases.

The Missing Side of Eviction Studies

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Last week the Lawyers’ Committee for Better Housing, a Chicago based nonprofit, released another study on evictions using Cook County data cross-referenced against census data. Their results can be found here. It’s a worthwhile study which is certainly of equal if not greater interest than the information presented by Eviction Lab, the National Law Center on Homelessness & Poverty’s PDF report on the interactions between eviction and homelessness, and Matthew Desmond’s seminal 2017 book on eviction.

These studies are all fantastic sources of data on the current U.S. eviction crisis. The researchers have all done some excellent work. But there’s a problem. They only focus on the tenant side of things.

A legal eviction is a five-party transaction involving landlords, tenants, judges, lawyers and the sheriff. It might also involve the police, the banks and the insurance companies as well. But for the sake of this article we’re focusing on the main missing party in all of these studies and data portals: the landlords. Continue reading The Missing Side of Eviction Studies

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Kay Cleaves

Founder and owner of RentConfident. She's the primary developer of the website and research engine code. She's spent over 10 years working in the Chicago rental industry and has assisted with over 1200 leases.

Twitter’s Opinion of Chicago Apartment Hunting

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In February of 2016 I ran an article where I searched through Twitter to see the adjectives that people used to describe their landlords. As it’s been a while I figured it might be good to go back and see what Twitter has to say about another topic. I’ve actually had this geographically restricted search running for a while now, sitting in my Tweetdeck and building up. The Chicago area Twitterverse has quite a lot to say about apartment hunting, and most of it isn’t good.

Here are the adjectives that were used in posts that mentioned apartment hunting over the course of roughly twelve months, filtered to exclude posts from property managers, agents and landlords.

Appearing Multiple Times
Stressful (5 times)
Difficult (Twice)
Frustrating (Twice)
My least favorite part about living in Chicago (Twice)
Overwhelming (Twice)
The worst (Twice) Continue reading Twitter’s Opinion of Chicago Apartment Hunting

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Kay Cleaves

Founder and owner of RentConfident. She's the primary developer of the website and research engine code. She's spent over 10 years working in the Chicago rental industry and has assisted with over 1200 leases.

Wolf and Jay: Two Landlords’ Approaches to a Troubled Neighborhood

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In January 2016, local Chicago newspapers ran the obituary of a Chicago landlord. His name was Jay Michael and he had died at the age of 34 after a long battle with non-Hodgkin’s lymphoma. He had made his name by investing in unused real estate in struggling neighborhoods. In October 2018, local Chicago newspapers ran the obituary of another Chicago landlord. His name was Louis Wolf and he had died at the age of 94 after years of failing health. He had also made his name by investing in unused real estate in struggling neighborhoods.

Michael’s obituary contains words such as “brainchild,” “creative,” and “forward-thinking.” Wolf’s is peppered with more sinister terms: “cautionary,” “ruthless,” and always in the same sentence with his name, “notorious slumlord.”

Two famous figures in the local rental industry, of the same faith, race and gender, working in the same neighborhood. One, born into wealth in the 1980’s is praised as a hero, although not without his critics. The other, born into poverty in the 1920’s, is condemned as the “worst landlord in Chicago history,” but was also a proud grandfather who is remembered by those close to him as a quiet and kind mentor. What can we learn about being a landlord from the divide between the two? Continue reading Wolf and Jay: Two Landlords’ Approaches to a Troubled Neighborhood

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Published by

Kay Cleaves

Founder and owner of RentConfident. She's the primary developer of the website and research engine code. She's spent over 10 years working in the Chicago rental industry and has assisted with over 1200 leases.