Chicago Property Management Blog

Coffee & Real Estate


We, at Landmark Property Management, offer full service commercial and residential property management for real estate investors looking to scale their portfolios. We’ve been in business for about 4 and a half years and have grown from 0 to almost 400 rental units. Our service area includes Chicago and suburbs in Cook County, Dupage County, and Will County. See the very bottom for a full listing of the areas we service.

When do you think an investor should hire a property management company?

This is going to be different for everyone - depending on your strengths and weaknesses, goals, etc. If you’re looking to be hands off and scale your portfolio quickly, the sooner you can give us a call and get us involved, the better. We are going to advise you on things like where to buy, what assets to buy, what return you can reasonably expect from a given investment, etc. We take as much of the work off your plate as possible to allow you to focus on the important things that will grow the portfolio quickly such as finding deals, sourcing debt, and raising private capital.

What are the usual problems that Landlords encounter?

We get a lot of calls when a tenant is moving out and the landlord doesn’t know how to properly market their unit for lease or screen tenants. We also get questions around evictions, the RLTO (Residential Landlord Tenant Ordinance), and security deposits. A lot of this stems from not properly screening their tenants. Filling out an application and having a quick verbal interview with the prospective tenant is not sufficient and opens you up to a lot of liability. We start our marketing process with professional photos, listing the property on the MLS, and syndicating the listing out to 80+ different websites, as well as working the listing with our in house leasing team. This allows us to cast as wide of a net as possible and bring in more qualified applications. We then run the applications through a thorough and comprehensive screening process to ensure the highest likelihood of that tenant performing (paying rent and taking care of the unit) over the length of the lease.

Residential Landlord Tenant Ordinance (RLTO)

The Residential Landlord Tenant Ordinance, also known as the RLTO, is a complex and strict set of laws that govern the Landlord-Tenant relationship in Chicago (Cook County has a similar set of laws called the RTLO, the Residential Tenant Landlord Ordinance). Not understanding the ins and outs of Chicago’s complex landlord tenant laws increases risk and puts you in the crosshairs of potential litigation. Here at Landmark Property Management we have the industry knowledge and expertise to navigate these laws along with the legal experts to handle any evictions and/or litigation.

How are maintenance requests handled?

Again, at Landmark Property Management, we are a full service property management provider. We handle everything so you don’t have to! Specific to maintenance, this would mean that the maintenance request would come directly to us and we would either send our in-house maintenance team or dispatch a third party vendor depending on what the issue is. If the call is after hours, it would be directed to our 24/7 Emergency Maintenance Line where someone would be dispatched to fix the issue and mitigate damage. As you can imagine, tenants want repairs done quickly so it is very important to respond to these requests promptly. Equally as important, making repairs expeditiously can prevent a small issue from turning into a catastrophe. 

Evictions & serving/filing notices

It is absolutely imperative to make sure you are serving the right notice to your tenants when beginning the legal process. Here is a great resource that sheds light on whether you should be serving a 5, 10, or 30 day notice. If it’s rent related, you can also check out our video blog here for some other tips and tricks. Once you’ve served the proper notice, you want to make sure you are hiring a real estate attorney who specializes in evictions in your area (this is super important as different cities, counties, and states have different laws). If you need a recommendation, don’t hesitate to reach out and we would be happy to introduce you to an attorney that we use.

Security Deposits VS Move In Fees

This is going to be a personal decision based on your appetite for risk as well as your local laws. In the City of Chicago, we absolutely do not hold security deposits. In places that are more landlord friendly such as Will County and Dupage county, we do recommend holding security deposits. Also, even though Cook County is very tenant friendly, they have what’s called a “right to cure” so we do still currently hold security deposits for our properties in Cook County, that are outside the Chicago city limits.

Do you recommend holding properties in an LLC?

Yes, I do recommend holding properties in an LLC. Whether you create a new LLC for each property or hold a few properties in each LLC, that is a personal decision based on your appetite for risk. If you are very conservative like myself, you can take it one step further and own your LLCs in a Trust. If you’d like to learn more about this, you can check out my video on this very topic here.

Outlook on the housing market, recession, real estate investing?

I do not have a crystal ball so this is certainly not investment or financial advice. However, I do believe we are already in a recession and we will continue to grind downward slowly for the rest of 2023, and possibly even into 2024. That being said, I don’t see that as a bad thing for real estate investing. The housing market skyrocketed almost 40% over the past few years and is coming off a 12 year bull run. The multi-family asset class, along with most other asset classes have been following a similar trajectory. That type of growth is unrealistic, unhealthy, and unsustainable. Relief is necessary at some point to give the market some breathing room. Due in large part to a rapid rise in interest rates, I believe we’ve finally reached the point that the craziness has stopped and valuations begin to retreat from their recent all time highs. As a real estate investor, you make your money when you buy. It has been very hard to make investment properties work when you are buying at historically high prices. This should allow buyers to pick up properties at a reasonable price and refinance at a later date when interest rates come back down. Right now, most sellers and buyers are still not seeing eye to eye but I feel like the longer we see rates at an elevated level, the more sellers will come to the realization that they need to value their property appropriate to the current market conditions. Recessions can be painful but there is always a silver lining. The silver lining that I am looking forward to is the opportunity to once again purchase good real estate for a reasonable price.

Named one of the Best Property Management Companies in Chicago, Landmark Property Management is a full-service brokerage with a reputation for going the extra mile for our clients. If you need help, have any questions, or are interested in learning from the best property management company in Chicago, don’t hesitate to reach out! You can contact us at Landmark Property Management via phone at 312-313-8553 or send us an email at

Full List of the Areas We Service

Chicago: Lincoln Park, Old Town, Gold Coast, River North, Bucktown, Lakeview, Lincoln Square, Albany Park, Irving Park, North Center, Avondale, Logan Square, Humboldt Park, West Town, Logan Square, Wicker Park, Ukrainian Village, West Loop, Downtown/Loop, University Village/Little Italy/Medical District, Pilsen, Bridgeport, Chinatown, South Loop, Bronzeville, Hyde Park, Woodlawn 

Cook County - Brookfield, Evergreen Park, Flossmoor, Homewood, La Grange, Oak Forest, Oak Lawn, Orland Park, Palos Hills, Palos Park, Rosemont, Tinley Park

Dupage County - Burr Ridge, Darien, Downers Grove, Elmhurst, Glen Ellyn, Hinsdale, Naperville, Oak Brook, Villa Park, Westmont, Wheaton, Willowbrook, Woodridge

Will County -  Bolingbrook, Crest Hill, Frankfort, Homer Glen, Joliet, Lemont, Lockport, Mokena, New Lenox, Plainfield, Romeoville, Shorewood