Two Apps for Chicago Renters with Problems: Squared Away Chicago and Rentervention

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I was recently contacted by the PR guy for a relatively new mobile/web app called "Rentervention". (Hi, Gordon!) He asked me to do a profile piece on the app, which I am doing today in conjunction with a somewhat similar app called "Squared Away Chicago". Neither of the sponsoring groups have paid me for this coverage, nor did I ask them to. But I wanted to get it out in the open right off the bat that this is probably tying in with someone's marketing campaign. So be it.

Logos in the header image are property of their respective companies.

In this digital age there's plenty of renters out there who shy away from talking to authority figures, doubly so when potentially controversial issues are at stake. In cases of landlord-tenant relationships the issues can be particularly thorny, ranging from simple problems like broken appliances to major ones like retained security deposits, illegal evictions and life-threatening conditions. The impostor's syndrome is real when you have to confront someone who probably knows the law far better than you do. If a landlord fails to respond to reports of trouble at their property, tenants are additionally faced with the potentially expensive and time-consuming prospect of turning to the court system.

RentConfident's apartment safety reports seek to inform you about severe, chronic issues with a landlord or building which have escalated to the point where they've been documented in government sources. These include problems such as foreclosures, housing code violations, bankruptcy filings and registered sex offenders living nearby. However, we cannot always discern from government data if a landlord is simply a poor communicator, or if smaller problems exist which may be severe, but not severe enough to merit attention from the city or county inspectors. We rely on tenants taking serious matters to the government if we're ever going to be able to include them in our reports.

Over the past six years, two homegrown apps have emerged to help Chicago renters communicate with their landlords when big drama problems emerge in their apartments. Both are backed by non-profit organizations. Both help renters shift problems from person-to-person communication into legal proceedings should such a step be necessary. However, each one takes the character of the organizations that created them, and each one works in a slightly different way. Today I'll be profiling both of them to help you decide which, if any, might best help you to get that broken thing in your apartment fixed in a timely manner.

Squared Away Chicago

Squared Away Chicago is a free app for mobile and PC browsers created by the Metropolitan Tenants Organization, with help from Greater Good Studios, Philamonjaro Studios and DevMynd on the tech side of things. It was released in 2014 at which time it was highly praised for its innovation. You can see the MTO's original press release here. A video from Greater Good Studios explaining the motivation behind the project can be seen below.

MTO Digital Campaign from Greater Good Studio on Vimeo.

The MTO is a Chicago-based tenants' union. They've been around for decades, formed during the era when the city was drafting the CRLTO. They're made up of community organizers and tenants, and most of their work is done direct-to-tenant via their hotline and direct-to-government through tenant advocacy campaigns.

Squared Away is not a downloadable app. You need either a phone with a mobile browser or a PC with a web browser to use it. At its core it is an intake route that allows the MTO to connect with tenants in need, but it takes the guise of a communications tool for both landlords and tenants to use.

Tenants who use the app can follow the prompts provided to properly document a problem and communicate it to their landlord. They can receive information on their rights under the CRLTO. They can also find a checklist for use on move-in day.

Landlords can also sign up to receive communications from their tenants about problems and tips for operating within Chicago's many rental laws. I'm guessing that this is targeting smaller private landlords who don't already have such a system in place.

If the landlord doesn't respond to a tenant's reported problem, the MTO will already have the problem documented on file so that they can step in and advocate on behalf of the tenant. The MTO is known for sending threatening form letters in lawyer-language to landlords on behalf of tenants with major apartment problems. Last I knew they charged a couple of hundred bucks for the letter writing service, although that was several years ago and their policies may have changed.


Rentervention is a free app for text messaging and PC browsers created by the Lawyers' Committee for Better Housing. I'm not sure who is handling the tech side of their project. It was released in March of 2019. You can see the LCBH's info about it here. A video explaining the app can be seen below.

LCBH is a pro-bono legal aid service and advocacy group for low-income housing in Chicago. They have also been around for decades, formed in the 1980s by attorneys who wanted to work with aldermen to improve the decrepit condition of the Rogers Park housing stock. They're made up of attorneys who work with low-income renters in courtroom situations and with city policymakers to create new legislation for rental housing.

Rentervention is a chatbot for tenants who have attempted to get problems fixed without receiving any landlord response. You need a phone that can send and receive text messages or a PC with a web browser to use it. At its core it is an intake route that allows the LCBH to connect their attorneys with low-income tenants in need of representation.

It walks you through a series of questions to figure out the nature of your problem, and then spits out a lawyer-language letter that you can send to your landlord to let them know that you're getting serious about problems in your apartment. Should a letter not be the proper course of action it can also send you to other city resources. If your case merits attention from an attorney and your income is suitably low it will connect you with one of the volunteer lawyers working for LCBH.

There is no landlord-facing side of the Rentervention app.

Comparison Time

When should you use these apps?

Squared Away Chicago can be used throughout your lease to look up your rights and document problems. If your landlord is already using it you can use it as well to communicate with them with the assurance that your communication attempts are being documented by an interested third party who can give you a boost should things go wrong.

Both apps can be used if a problem goes unresolved for a lengthy amount of time despite your attempts to contact your landlord in writing about them. Squared Away Chicago can escalate these problems to a grassroots tenant advocacy group. Rentervention can escalate them to a licensed attorney.

Who is the intended audience?

Squared Away is targeting Chicago renters and small Chicago landlords who do not have their own in-house repair tracking systems. Rentervention is only targeting tenants. As far as I can tell both services are offered only in English. Use of Squared Away requires more technical savvy (phone based web browser) than use of Rentervention (text message), but the difference is minimal.

Who is bankrolling the apps?

Both MTO and LCBH are Chicago-based non-profit groups which emerged at about the same time and in the same area of Chicago. They're both well-established and respectable tenant advocacy groups although MTO has a more blue-collar approach while LCBH takes the white-collar route.

What is the likely outcome of using the apps?

You will probably get a follow-up call or email from the sponsoring organization to find out how things are progressing with your case. Your landlord may be intimidated by the letters or may shrug them off. Larger landlords are far more likely to shrug them off as most of them get quite a lot of similarly angry and official-sounding letters. I doubt that they'll increase your chances of winding up in court, although their goals of helping you to properly document problems may increase your chances of winning a case should the matter go that far. They may increase your chances of your landlord raising your rent or failing to renew your lease even though such practices are retaliatory and illegal.

Closing Thoughts

Here's a fun story about the MTO. At the property management company where I used to work, we'd occasionally receive letters from them on behalf of our tenants. The initial reaction was not one of intimidation, since my boss (the landlord) was an attorney and more annoyed than freaked out by legal language. Rather, he'd react with a sort of sadness that another tenant had been "swindled by the MTO" into coughing up a couple hundred bucks for a fancy pack of lawyerese letters when a basic plain English letter would have served just fine. Usually the broken item was something already on our list to fix, although we may have admittedly been slow in getting to it. The letters themselves would accuse us of hundreds of problems, most of them false accusations, in hopes that something in them would stick should a court case become necessary.

Here's another fun story about the MTO. 9 years ago I contacted them about helping out with their Tenants' Rights Hotline. After interviewing me they decided that my opinions were too balanced between landlord and tenant to be a good hotline staffer. They suggested that I instead contact the landlord support group Community Investment Corporation since I apparently liked landlords so gosh darned much. I wound up spending the time I would have spent volunteering at MTO making RentConfident.

This is not to knock them, they do good and necessary work. The CRLTO would not exist if it weren't for the MTO. When tenants contact me with landlord problems I'll frequently send them over to MTO since that isn't really my wheelhouse anymore. If you're a low-income tenant with a problem there's very few groups that will fight harder for you and they fill a necessary space within the industry. I'm sure there's plenty of landlords out there who do respond more promptly when a bunch of lawyerese letters show up in the mail. However, I worry that they may have burned too many bridges with the landlord community in Chicago for the landlord-tenant communication part of Squared Away Chicago to ever be utilized to its full potential. It's a great app with good intentions but possibly backed by the wrong company.

I suppose I should also toss in a fun story about the LCBH. Very early on in the development of RentConfident I reached out to their Legal Director (now their Executive Director) for some guidance on a rather sticky matter within our reports and how it would hold up under the then-recent Supreme Court disparate impact decision. He pointed me in a good direction. I've sent some tenants in need of legal advice over to them from time to time as well.

It may seem from all of this that I take a dimmer view of MTO than I do of LCBH. This isn't necessarily the case although I can't deny that there's probably some bias rattling around in me somewhere. I'm attempting here to weigh the two apps independent of their sources but given that each one serves a dual role of a communications tool and a customer acquisition route, it's impossible to completely divorce the apples from their respective trees.

Rentervention has a far narrower focus than Squared Away Chicago. The chatbot/SMS route is an interesting one and will probably appeal to a larger audience, but the narrow window when its advice is useful will limit said audience. I'm very glad that there's a second digital option available now, as foot-dragging landlords are always going to be an issue and renters aren't getting more capable of face to face negotiations as time goes by. I think there's room in the market for both of them, and as the outcome of their use inevitably becomes part of RentConfident's data supply chain I'm grateful that they both exist. I wish both of them had options for languages other than English, but then I wish RentConfident did too.

Given the choice, which app would you use? If one of the two were to roll out coverage to your city, which would you prefer? If you were given the choice between talking with your landlord directly or using an app, which would you prefer to use? For the landlords out there, do you find that you respond to attorney-authored letters more rapidly than letters from other tenants? Let me know in the comments or at RentConfident on Facebook or Twitter!

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Kay Cleaves

2 thoughts on “Two Apps for Chicago Renters with Problems: Squared Away Chicago and Rentervention”

  1. If these apps were available in Greater Boston, I would likely utilize Squared Away due to my personal rentor profile. I do not fall into Rentervention’s demographic. I think the service provided by Rentervention is invaluable, and I would welcome it in any city. Both should strongly consider expanding their reach with a multilingual platform.

  2. Thanks for promoting Squared Away. We view it as tool that helps tenants to communicate with the landlords and to document their situations in writing and with photos. Thanks for your work. -And yes we would love to make it bi-lingual.

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