Buying and selling

Well, we’ve crossed the finish line. Just two months ago, Kelly and I closed on the sale of our city condo and unlocked the doors to our new 1924-built home in suburbia.

If you’ve ever been in a similar buying-and-selling scenario, you know how emotionally trying of a time it can be. Early on in our decision process, we thought very hard about whether we should try selling ourselves to save money. We’re both pretty DIY-minded people, so the challenge seemed to make sense. But, as we got close to actually making a decision, the prospect of climbing that mountain with everything else going on seemed insurmountable. In the end, we decided to sell through Redfin and buy using a personal friend of Kelly’s who already lives in the suburb we’ll be moving to.

The whirlwind sales process

We invited our Redfin agent over to get us up to speed on what it would mean to sell our condo. After listening to a bit of a sales pitch, we were given a 30-day timeline that would get us to listing day: de-clutter, deep clean, take photos, list!

By the next day, she’d already decreased our timeline to two weeks to make sure there were still some summer buyers left on the market. We would rent a storage unit, hire deep cleaners using Groupon, and used Kelly’s mom’s Tahoe to move extra clothes, curtains, pillows, and all the Ikea furniture we bought when we moved in.


My favorite moment came on picture day. A day-long storm ripped through the city, so lighting was terrible (I ended up having to take exterior photos myself using a wide-angle lens I bought for my iPhone). I drove a Zipcar home from my office downtown—through streets that I’d hear later had completely flooded over—only to be told when I got to the drop-off point that the photographer still had two hours remaining to conduct a 3D scan of our apartment. For a self-proclaimed, but seldom-proven DIYer, having a 3D scan of a place I’m looking to buy would be a HUGE selling point. I ran barefoot through the rain to the bar next door and, after borrowing a couple of dish towels from the bartender to dry off my feet, settled into a few beers while the photographer finished up.

As a side note, you can’t be in the home during the 3D scan because any movement will throw the whole process off. Our time at the bar was mostly spent praying that the cat wouldn’t mysteriously show her face, scare the photographer, and ruin everything. She didn’t, and the scan turned out great.

We listed two days later on a Thursday, and had our first open house on Saturday. Open houses are excellent, unless you’re the homeowner. You’re nervous every moment prior to, during and after that miserable two-hour block. If you have a pet, and especially a cat, you need to figure out how to mask the fact that she exists and has lived with you for two years. That’s in addition to meticulously scrubbing everything that’s not the right white, off white, gray or light brown that it’s supposed to be plus vacuuming every surface, everywhere.

We had to buy Pepper a small dog-training crate because she was getting cabin fever in her smaller cat carrier. In just the few times we took her out for open houses and showings, she became very comfortable with the car and made the area under the front passenger’s seat her new bed.

After our first open house, we received zero showing requests in the first week. Not only were we disappointed, but we began feverishly checking the analytics on our property page online. We looked at how many people were viewing our listing and how many favorited. And, we kept comparing our views to where the condo had been a few years previously when we bought it. Within seven days, we lowered the price and set up a second open house for the final Sunday in June, our second full weekend on the market. Our agent scheduled the open house for the afternoon, but there was one huge problem. We live a block south of Halsted and Diversey, and the Pride Parade started at noon. Although there were two requested showings to happen after the open house’s conclusion, both cancelled in lieu of the festivities. Totally legit.

But then, about midweek, real showing requests started rolling in. Every morning, the ritual was the same. Wake up too early. Get Kelly out the door and off to work. Clean everything. I left a set of keys in the garage in case a random day showing popped up, which it never did. That week, we may have had five showings. On Thursday, July 3, we got an offer—exactly two weeks after we went on the market—and on July 4 we contractually declared our independence from the city.


Once you sell your place, you have to leave. Sure, you have 45 days to close, but you’ll need to go. By this point, we still hadn’t seen any homes we would feel proud to own. While contract negotiations finalized on our condo, we started looking in earnest for a place to live (yes, we got a lot of jokes about being homeless). It seemed hopeless for a few days—we’d seen everything, we felt—close to 30 homes! But then a glut of new homes came on the market. One in particular stood out to us, and Kelly stayed out after work and made a drive-by. I commuted out to the suburbs the next night, saw it, and we were ready to make an offer on Friday. This happened just a week after we’d started our sale process on our condo.

The selling agent turned out to be a bit of a peach (from our perspective). He scheduled overlapping showings, which felt like a skeezy tactic to boost interest and appeal. After we offered, he seem really uptight about us being contingent (“Oh, you mean you don’t have enough money to have two mortgages?”). Then, after we busted our butts to get him all the paperwork he requested, he went dark for the entire weekend. Offering on a beautiful home and not hearing a word from the sellers for four days—not to mention knowing that showings are still going on—is like being in a cage you don’t have the keys to. The owners know they have the upper hand, and they seem happy to keep things that way for as long as possible.

Inspection day

In the end, we got the house. My parents were in town for the weekend of the inspection, and Kelly’s family accompanied us too. I’ve never been happier to have so many cooks in the kitchen. The fireplace was not set up to work or inspect, and the furnace had a condensation leak. Additionally, it looked like the sellers had closed all of their second-floor duct vents (in summer?), causing condensation to form on the ducting and get absorbed into the ceiling, in one particular place above the kitchen. Mostly, the inspection revealed the home was a great buy in a spectacular neighborhood, and even though we finalized the details of our offer more than a week and a half after we sold our condo in the city, our attorney helped us negotiate a same-day closing, meaning we didn’t have to hold onto one mortgage longer than the other, and our moving and storage fees would be (relatively) minor.


Probably the most trying part of this process was waiting for the closing day to come. Yes, there’s lots of moving to be done, but 45 days can feel like a long time when you’re anxiously anticipating the end. Reflecting on the process, we hired real estate agents because we felt it would lower our stress and anxiety levels enough to successfully manage the transition. While it seems like we’re doing that, buying and selling is a stress and anxiety inducing practice, no matter how much help you enlist. I’m happy with our decisions, and I’m happy we chose a move-in ready house instead of a fixer-upper. At this point, there’s nothing I want to do less than begin more projects the moment I move in (except maybe in the backyard).

I hope you’ve found this somewhat insightful. If you’re looking for help figuring things out for yourself, don’t hesitate to leave a comment.


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