I’ve Got 99 Problems and Real Estate is One.

What to Do When You Struggle with Real Estate
Jennifer Lake Confete Tulle Gown
Dress: Confête Pink Tulle Tiered Gown | Bag: Neely & Chloe x Ariel Okin Bag | Shoes: Bella Belle Florence Embellished Pumps | Jewelry: Confête Crystal Fringe Earrings | More details of our family room design here

Confession – I suck at real estate. Clearly it’s not my full-time job nor am I am a licensed broker. But in my “dream” scenario, I’m wheeling and dealing with the likes of Josh Flagg and Tracy Tudor. The offers, the contingencies, the negotiations – oh my! 🙂 But no, that’s not my actual reality.

Keep in mind I’ve only been a part of five real estate deals in my entire life. Yet, give me a single episode of Netflix’s Selling Sunset, Bravo’s Million Dollar Listing franchise or a single viral SNL sketch about real estate, and you’d think I’m the next Frederic Ecklund. Le sigh.

Obviously that’s not the case. Haha.

Instead, we’ve simply been in an active search for a home. No, not a new main residence, but a second home that would serve as a small getaway for us, our family, and close friends. For as long as I can remember, buying a lake home has been a dream of ours. In fact, when we bought our Chicago home, we carefully budgeted knowing we’d want to invest in a second property down the road.

However, the journey has been much longer (and harder) than we imagined.

Our Current Real Estate Reality

Much to the (understandable) chagrin of our actual real estate agents, I treat the process exactly as you shouldn’t – emotionally. When something falls through, my heart is in my throat. In fact, there was one distinct conference call with our agent when I’ve asked Bob to take the lead. He’s SUPER level headed in high-stress personal situations. I, on the hand, am not.

Jennifer Lake Pink Ruffle Dress

Lesson #1 of real estate: don’t get emotional. I know that fact but phew – it’s tough. 🙂

Listen, we are incredibly fortunate to be in a position to even consider a second small home. There are moments when I step back and thank my lucky stars that we’re able to think about the option.

At the same time, we aren’t crazy affluent. Moreover, we’ve had to work for everything that we’ve done (as I’ve mentioned in my marriage or mortgage blog). Our families don’t provide any ongoing financially support (nor should they). There’s no cushy safety net, family trust, nor windfall coming our way.

So, it’s scary. Super scary. Any decision we could make is a big risk, and we’re cognizant of that. But we want to try. First, we’ve saved, saved, saved. Plus, we’ve both worked full-time for two decades. So, if buying a second home financially makes sense, we’ll try to make it happen. Carefully. 🙂

Say Hello to Your Fellow Zillow Expert

Each morning, I wake up to piping hot cups of coffee, I check my work email and Microsoft Teams… then, I swiftly head to the real estate apps.

Forget Captain Crunch or Fruity Pebbles, Zillow, Redfin, ZenList are my go-to breakfast. One by one, I check my saved and new searches for the perfect hidden gem. That once-in-a-blue moon property that sweeps me off my feet in a Renee Zellweger, Jerry MacGuire like moment, “You had me at hello.”

Jennifer Lake Living Room

You know, that property that screams, “This is your future. Welcome home.”

Hot Market, Fast Deals

Are you like me when it comes to Zillow and real estate searches? I can’t get enough. From assessing local comps to scoping out stunning custom homes in exotic locales, it’s beyond addicting. Plus, with interest rates so low right now, it’s smart to strike while the iron is hot.

At the same time, the market is CRAZY. Like positively insane. Properties are snatched up in the blink of an eye and all-cash deals with no contingencies are the new normal. Plus, the places people choose to move are changing (as I mentioned in my Illinois exodus blog).

The past year, our real estate search became more serious. We started attending open houses, scheduling one-off tours, and spent weekends driving around the potential areas in which we’ve been interested.

It’s been fun! But again… the market is NUTS.

Crystal Drop Earrings

How wild? Well, Crain’s Chicago Business released an article that said, “The top of the market just went over the top,” with stats that say 75 homes in the Chicago area alone have sold for a $4 million or more. Wowza.

Small lakeside cottages? The industry is even crazier. Our agent has told us for years, “move fast or you’ll lose it.”

Buying a Second Home

A couple months ago, we stumbled upon what we thought could be “the one.” After seeing photos online, we scheduled a tour within 24 hours. After touring, we knew it was a phenomenal option. The budget was right (small, fixer-upper) and a reasonable distance from Chicago. We were over-the-moon thrilled!

Since our budget is modest for a waterfront property, I was especially excited at the price tag. Sure, the home required a ton of work. But it had decent bones and could be a project for us over the next decade.

After leaving the tour, we headed to dinner to discuss our offer terms – how much we’d offer, contingencies (we are not, nor will ever be, an all-cash offer, haha), closing dates, etc. We left the restaurant with an air of excitement.

We called our agent and told him our offer terms. It was off to the races!

I distinctly remember our drive home and looking up at the sky feeling elated about the possibility of a new chapter. We held hands the entire drive home. I could tell Bob was just as excited…

And then we got the call.

Buying a Second Home – The Call

“They accepted an all-cash offer and the home is already pending. I didn’t even get to submit your offer in time.”

Wait… what?

Yep, within a couple hours, our potential vacation home was gone in a flash. An all-cash, above-ask offer with no contingencies came in and our agent hadn’t even had time to write up our offer. We would have lost it anyway against the other deal terms. Moreover, at “pending” status, it meant the home was truly gone. The deal would not be “falling through” so we couldn’t even be a back-up.

Remember how I said Bob needed to take a call with the agent vs. me? This was the one. He was so level-headed.

I was speechless. I was SO sure that was the one.

Not going to lie, we’re still really sad about it. But when the time comes, we’ll find the right place.

Alas, the search continues.

Jennifer Lake Pink Tulle Ruffle Gown

Feel Grateful

As 2021 comes to a close, I am feeling utterly thankful. We have our health, a house we’ve made a home, family we love, and steady jobs. It’s a great privilege to have all of these things, not to mention the ability to consider buying a second home. As mentioned earlier, it’s something we’ve dreamed of for years, and we know it will prove to be a place where wonderful memories will be made. Excited to share more as we keep moving forward!

Dress: Confête Pink Tulle Tiered Gown | Bag: Neely & Chloe x Ariel Okin Bag | Shoes: Bella Belle Florence Embellished Pumps | Jewelry: Confête Crystal Fringe Earrings | More details of our family room design here

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