6 lessons I learned the hard way about working with contractors
From homeowners to condo board members, do these things early to avoid home repair and multi-unit contractor nightmares later
This has been updated with a sixth lesson since its original publication date on August 8, 2025.
When the condo board phone number rang, I looked at the caller ID in confusion. Why was our insurance company calling us? Within a few minutes of conversation, I found out that one of the condo owners claimed a bucket on our roof had fallen onto his windshield and cracked it. He was blaming the roof repair company for being irresponsible. I rolled my eyes and assumed he was lying about the contractors we’d hired. Where would this magical bucket come from anyway?
I immediately walked outside to find his car, which was gone. For a couple of days, I didn’t see the car. Now how am I supposed to take pictures of car damage as a board member if I can’t find the car? (To make matters worse, he and I did not get along — at all — and he and another condo owner were constantly accusing the board of not handling roof “damage.” While we were scheduled to have an annual roof inspection, the ring leader convinced the car owner that we needed a new roof altogether without any proof.)
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A couple of days later, the car did show up and the windshield was indeed cracked. I winced and sympathized with the car owner. I contacted the insurance company again after taking photos of the car. But there was still the matter of proving that the car damage came from the roof repair company leaving a bucket behind and not a car accident away from our property.
While there was a veiled accusation that the bucket was purposely thrown onto his car, there were two problems with this maniacal idea: 1) If someone climbed onto the roof to throw the bucket, how can they control gravity once a bucket is pushed? 2) Who would risk their own car (mine parked next to his) potentially getting hit after throwing the bucket, specifically considering our parking lot was full the whole week?
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I walked into the boiler room, rewound the cameras to a specified date and learned one of the five biggest lessons about working with contractors that homeowners will ever need to know.