Into the Weekend 9.4.26

Into the Weekend 9.4.26

  • Brad Lippitz
  • September 4, 2026

Into the weekend!

One of my favorite things about growing up was missing school when I was sick. I would go to great lengths to try to increase my fever (even faking the reporting of the thermometer’s reading to my mom), cough really loudly at every possible moment (combined with the occasional hack), spend hours in the bathroom privately coping with the unbearable diarrhea (not! rofl!), and feign constant and extreme dizziness and nausea. The goal was to protract the “illness” as long as possible to ensure I got to stay home and do my favorite thing in the world:


Watch game shows on TV, non-stop, all day long.


In a strict household which limited the kids’ regular TV watching to an unbearable and grossly unfair one-hour-per-day rule (while my parents joyously enjoyed the unlimited watching rule which they so graciously bestowed upon themselves), staying home sick provided us the relief we kids so desperately coveted: to watch as much TV as we wanted.


During those glorious home sick days, I quickly became the world expert of “The Price is Right,” “Family Feud,” “Match Game,” “The Newlywed Game," ”The $10,000 Pyramid,” and “Wheel of Fortune” - which, looking back, honestly explains my off-the-charts acumen in today’s daily Wordle: “Pat, I’d like to choose an S,T,R,L, and an E please,” the necessary combo in the “Wheel of Fortune” bonus round most likely to help the contestant garner the big prize. 


But, looking back, the one game show which explains choices in today’s real estate market best was “Let’s Make a Deal!” where Monty offered the audience players the option to trade items, cash, or small prizes they already had for hidden mystery prizes behind curtains, inside boxes, or in envelopes. 


Do you trade in the $100 bill you already have in hand for what’s in the box that Johnny is bringing down the aisle (which, when uncovered, could be really anything: either a bag of Purina Puppy Chow… or a gift certificate for a brand new Oldsmobile Vista Cruiser with moonroof!!)? Or, do you trade in the $200 you have in hand for what Carol Merrill will soon reveal behind the curtain - which could either be a box of macaroni and cheese….or a BRAND NEW COLOR ZENITH TV with remote control!


Do you keep the known product - or take the risk for something that could be anything from way better to way worse?


I have clients who, after an exhaustive search with me and my team, finally narrowed their focus to a specific layout, on a specific tier, at a specific height, in a specific building. With nothing on the market meeting those - shall we say “specific” criteria, my team and I went to work and pounded the pavement for our clients. After months of hardcore off-the-market canvasing, searching, begging, and bribing (no, not that, silly!), we finally were able to locate the PERFECT off-market opportunity. Exactly what they wanted.


But when we finally toured (THE PERFECT) condo, the only thing our noise-sensitive clients could focus on was the barks of the dog in the neighbors’ apartment when someone was entering or leaving the condo. 


Although we did ultimately go under contract on that condo, the deal became doomed when the sound engineer they hired came up short with solutions to protect my buyers from the barking. And, unfortunately, we learned that the dog was only three years old - and, also unfortunately, accidentally poisoning dogs or pushing them off balconies could lead to imprisonment for a long time, a sacrifice even I was unwilling to make for our clients.


So, the thing is you never have any guarantee when you buy a condo: who lives next door, who might live next door when that unit sells, what kind of animals they have, instruments they may play, or even if they may have a gaggle of rotten young kids crying, screaming and carrying on at all hours of the day and night.


Of course, there are condo rules which limit many activities of its residents. But so many activities are just dangling out there outside the purview of the stated rules - and the law. 


So, with absolutely no guarantee, do you take the unpleasant - but known - barking dog...or do you risk the unknown of what you may discover after you close - immediately or even in the future.


I know it goes against today’s (truly insightful) lesson… but I always chose the box that Johnny was bringing down the aisle. (Cough, cough).


Have a great weekend!


Best,

Brad

Things to do this weekend...

Chicago Jazz Fest

Dates: September 4 - 6

Time: Times Vary

Location: Millennium Park

A Chicago tradition for more than 40 years, the festival attracts musicians and music fans from all over the world to lakefront Millennium Park for four days of unforgettable live jazz performances.

The Great American Lobster Fest

Dates: September 5 - 6

Time: Times Vary

Location: Navy Pier

Sink your claws into fresh Maine lobster flown in daily from the east coast, sip on ice-cold drinks, browse craft vendors, and jam to live music performances, all with Lake Michigan and the Chicago skyline as your backdrop.

Taste of Polonia

Dates: September 4 - 6

Time: Times Vary

Location: Copernicus Center (5216 W Lawrence Ave)

The largest and oldest Polish festival in the USA features nonstop live music, captivating dance performances, authentic Polish cuisine and beer, engaging exhibitions, local vendors, and a dedicated Kids Zone with a variety of exciting activities.

Bike The Drive

Date: September 6

Time: 6:30 AM

Location: Butler Field in Grant Park

Grab your bike and reconnect with friends and family on DuSable Lake Shore Drive. With sweeping views of the lake and skyline, you’ll enjoy fresh air and the wind on your face! Ride as little or as much of the 30-mile course as you’d like, and then enjoy a post-ride festival in Grant Park.

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Modern. Vintage. Architectural. Cool.

And everything in between.

Thinking of Buying or Selling a Home?

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Check out previous "Into the Weekends" on our website here.


Check out our new flipbook containing the past 6 years of Brad's musings here!

Compass RE is a licensed real estate broker. All material is intended for informational purposes only and is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to the accuracy of any description or measurements (including square footage). This is not intended to solicit property already listed. No financial or legal advice provided. Equal Housing Opportunity. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions.

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