Short Term Rental, Marketing/Furnishing – The Chicago Cusader

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Left: Living room (Before) Our focus was on keeping our Gary home simple and easy to clean, while retaining my parent’s aura. Right: Living room (After) Interestingly, I found that it was often cheaper to buy new furniture than to have old furniture restored. However, some pieces had become synonymous with the house being a home and was kept after various degrees of restoration.

Almost two decades ago, as my mom flirted with the idea of moving into a senior’s residence, a Gary realtor suggested that we sell my parents’ home and not keep it as a rental. She warned us that renters can be very hard on property and working with them can be very difficult.

A decade or more later, after the passing of my mom, the Gary rental environment has changed, somewhat. The expansion of the short-term rental industry and the opening of the nearby Hard Rock Casino Northern Indiana, gave us reason to keep the home and convert it into a short-term rental.

However, Ethel Rock, who we introduced in the fourth article in this 10-article series, decided not to deal with the consistent involvement with guests that short term renting requires. Instead, she chose to long-term rent her four, one-bedroom apartments in Omaha.


“I have rented to Section 8 clients and they haven’t been any different from the others,” she said about her residents in “The Climmie.” However, with college student renters, she has had trouble with renters subletting to others and the tenants having parties.

Recalling getting rent payments from the government during the height of the COVID-19 pandemic when there was a moratorium on tenant rent payments, she concluded, “I prefer Section 8 renters, because it’s guaranteed money.”

From her Metro DC base, Rock uses Zillow to screen tenants 1,200 miles away. “They do background checks, income verification, and credit checks,” she explains. The prospective tenant pays the charge.

Rock’s experience opened the door to our renting the house in Gary, but our plans to occasionally visit home reenforced our wanting to enter the Gary short-term rental market. (Since turning my Washington, DC basement into an Airbnb unit about ten years ago, the short-term rental industry has expanded with short-term rental conventions and with more insurance companies altering and creating products just for short term rentals.)

While Rock uses Zillow to attract and screen tenants, we use Airbnb, Vrbo, and Facebook. With Airbnb, we can see a little about the prospective guests, deny or accept them, and payments are guaranteed via the platform. Afterwards, the platform allows guests to write a review about us and we about them.

Airbnb charges hosts a modest fee for their services and comes with free insurance that some short- term rental insurance providers find fair, but woefully inadequate.

Via short term rental insurance specialist Proper Insurance’s website and agents, I have learned of the higher risk owners take when managing short-term rental properties. However, I also learned more about mitigating those risks and the limitations of home rental endorsements offered by legacy home insurance carriers.


Our Gary location is ripe for short term rentals. The newly renovated home is five minutes from the Hard Rock Casino and I-80/94; 10 minutes from the Gary/Chicago International Airport and I-90; and less than 20 minutes from I-65 and the Indiana Dunes National Park. The casino is the highest ranked in Indiana in terms of revenue generated. The airport ranks third in the state in the movement of freight.

Metro Washington, DC urban planner and educator Howard Ways advisees that promoting Gary’s proximity to Chicago should be a part of our marketing efforts. He recalls that during one job interview he similarly suggested that Wilmington, Delaware position itself as a part of Greater Philadelphia. Though traditionally seen as separate metropolitan areas, “one of the advantages of Wilmington is its strong transportation connection to Philadelphia,” he explained.

“From downtown Wilmington to downtown Philadelphia is 30 minutes by public transportation. A similar distance traveled from New Jersey (parts which have been traditionally considered suburban Philadelphia) to Philadelphia would take an hour by car,” he added. In many aspects, Baltimore has capitalized on its lower cost of living compared to DC, while promoting its proximity and transportation links to the nation’s capital.

Even with the Chicago/Gary region’s increased activity, our childhood home remains on a quiet street surrounded by the same woods where we played. Our remodeled home is a fusion of a typical steelworker’s home with original hardwood floors; three spacious and renovated bedrooms; modern open kitchen, dining room, living room and 1.5 bathrooms. We are also upgrading the basement, with washer and dryer, and an two-car garage with an electric vehicle charging station.


Unlike Rock, because we are in the short-term rental business, we had to furnish our space. Aside from renovating the structure, furnishing was another effort.

When creating a modern, but traditional setting inside the renovated house, the first decisions centered around what furniture to keep. Interestingly, I found that it was often cheaper to buy new furniture than to have old furniture restored. However, some pieces had become synonymous with the house being a home and was kept after various degrees of restoration including a more than 60-year-old dining room table that seats six and a stereo with an eight-track player, turned credenza.

Most of our shopping was online with the help of some of my nieces including one who operates two short term rentals in Florida. Our focus was on keeping our Gary home simple and easy to clean, while retaining my parent’s aura. Even when it came to linen, along with new, mostly white comforters, we decided to offer colorful, unique, well-kept Afghans, hand crocheted by an aunt and a sister.

As the contractor continued to craft the house into a renovated home, I slowly soaked in the monetary, time, and mental investments we were making for a single home. The anxiety of the risks was salved as I took a look at larger private investments in Gary, the type I had seen in Washington, DC’s slums  that blossomed into gems. In the next article, we talk to top players leading the renovations of one of those blossoming gems, Gary’s historic Union Station.

Next: Cast Down Your Bucket Where You Are: Renovating IN Gary, IN – Non-Profit/Cultural Investors

Gary. Steel Strong.

Gary native Wayne Young is the publisher of Port of Harlem magazine. Founded by Young in 1995, the magazine is inclusive, diverse, and Pan-African. He is also president of the Port of Harlem Gambian Education Partnership, which funds and manages small projects centering around culture, education, and community in the West African nation. He recently repurposed his parents’ home in Gary into a short-term rental.

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