Chicago Property Management Blog

Once again Investors in Chicago are going to have to pivot their business operations or even the entire model with the new rules that went into effect June 1, 2021.  This time the changes are for property owners that are renting out their condos, apartments, and homes to short term guests such as properties on the well known AirBnb and HomeAway platforms.  With this new regulation, the City Of Chicago is requiring the short te...

Numerous landlords harbor inquiries regarding Section 8 and the intricate details of the Housing Choice Voucher Program (HCV). Unfortunately, these intricacies vary slightly across different states, counties, and even cities. While the disparities between Section 8 housing programs are not substantial, it is crucial to align yourself with a Property Manager or fellow investor to ensure you avoid the pitfalls when considering a Section 8...

You hear everywhere how the housing market has a shortage of houses for sale and huge buyer demand. For someone getting into house hacking, the search can prove even more difficult. Just finding a two-, three, or four-flat building to house hack can prove super difficult. When you do find something, affordability becomes a factor because, real talk, Chicagoland has a pretty high cost of living. You may find yourself wondering how should...

If you’ve thought about becoming a property investor, you may have had concerns about startup costs. Maybe you worried over how long it would take to have renters pay the bills for an otherwise empty house. House hacking can give you an easier entry point into property investment and a place to live. While not a new concept, house hacking has quickly become a big topic in Chicagoland, even in the current seller’s market...

As an investment property owner, you want to maximize your return on investment. On the surface, short sales can look like an attractive way to get investment property at basement bargain prices. Getting a house for far less than market price can make solid investments, but of course comes with strings attached. Below, we discuss how to win at investment property short sales in Chicagoland. Short Sales ExplainedProperty owners find...

Last year, I had the opportunity to sit down with Andrew Chen, owner of Hackyourwealth.comAndrew is well known for his wealth building hacks and has been involved in some pretty interesting careers, some in which he had no prior training in at all. His content has been published on Forbes, CNBC, Business Insider, and Glassdoor. https://hackyourwealth.com/managing-rental-properties-property-management-tipsThis podcast in particular ...

Andrew Holmes is one of the most well-known names in Chicago Real Estate Investing. Andrew explains his incredible journey, from his early days as a hustling agent, to how he structured his first few investment deals. Andrew dives into specifics on how he finds deals, what attributes he looks for in an investment property, how he underwrites properties, and how he teaches others to scale. There is so much to break down here it’s a...

I have flirted with the idea of this article for quite some time now because I do truly believe in the use of Property Management from the investor standpoint. However, my hesitation in publishing this topic has been countered by the idea of the negative feedback I may receive for my comments below.   To head off some of those comments I will start by saying there are plenty of poorly run Property Management companies across t...

Chicagoland is home to an enormous real estate market that includes an equally large amount of sub markets. Anthony Citriglia, of Essex Realty’s, has a submarket that covers many of the near north and near northwest suburbs. Here he breaks down exactly what those markets are like, how they differ from the actual city of Chicago, and how they differ from each other. Following the post-war boom, cheaper access to cars and the d...

As investors ourselves, throughout many markets and class types, our primary goal is to attract and retain the best tenant possible for our properties.The “Best Tenant” can be defined by qualifications on their application, potential willingness to stay for a longer term, and/or ability to be a satisfied resident when we, as the Landlord, successfully perform the duties as required by the lease agreement. (We try to avoid hi...