Real estate investing is often painted as a straightforward path to financial freedom. Read a few books, watch some YouTube videos, take a course, and boom—you’re on your way to building a portfolio that prints cash.
But in reality? It’s not that simple.
Challenges, setbacks, and unexpected obstacles are part of the game.
And if you don’t have strong conviction about your goals, your strategy, and the market you’re investing in, it’s easy to get discouraged.
Let’s talk about why real estate investing is harder than it looks—and why it’s so important to be in it for the right reasons.
The Illusion of “Easy” Real Estate Investing
Books, online courses, and gurus make it sound like buying properties, renting them out, and making money is a plug-and-play system.
They downplay the reality of what happens when things go wrong—because they will go wrong.
I’ve been investing for years, and I’ve faced my fair share of challenges.
What separates long-term investors from those who quit is how they handle these tough situations.
Without conviction, those first major setbacks can make you throw in the towel.
So, let’s get into some real-world examples of what these challenges look like.
Wrecked on Rutherford: A Lesson in Perseverance
One of the most challenging properties I’ve ever owned is my house on Rutherford Street in Detroit.
At first glance, it seemed like a great deal—vacant, but rent-ready. I thought it would be a simple case of placing a tenant and collecting rent.
Oh, how wrong I was.
From the start, I ignored red flags.
The house didn’t look quite as good as the listing photos, and there were signs of rushed workmanship.
But I was eager to keep moving toward my real estate goals, so I pushed forward, bought the house, and figured I’d deal with any issues later.
That was a mistake.
The Problems Piled Up Quickly
- The handyman I hired turned out to be a con artist. He took my money, did little to no work, and strung me along for weeks.
- A break-in left us scrambling to replace a stolen furnace and water heater.
- My wife hit a breaking point, in tears, saying, “Sell everything. We’re done.”
- Later on, a sewage backup led to a massive insurance claim and a full gut of the bathrooms.
For months, this house was nothing but stress. But we pushed through, got it rented, and over time, things stabilized.
Today, it’s fully refinanced, cash-flowing, and worth nearly double what we paid.
Time has a way of fixing real estate problems—but only if you stick with it.
The Detroit Short-Term Rental Vandalism Nightmare
More recently, I faced a different kind of challenge at my short-term rental in Detroit.
Just two Fridays ago, I was getting ready for bed when my Ring camera alerts went off.
At first, I didn’t think much of it. It often picks up cars driving by or people walking their dogs. But when I glanced at the footage, I knew something was off.
Three people ran up to the house and spray-painted the doorbell camera.
Then, they went around back and did the same to the rear camera. Unfortunately for them, they didn’t realize there was a floodlight camera high up on the house that caught them in the act.
When they spotted it, they ran off.
But the damage was done.
What Happened Next
- They vandalized the property, spray-painting the brick, smashing windows, and damaging the doors.
- The police arrived within 20 minutes, secured the home, and made sure nothing was stolen.
- Two nights later, the vandals returned and caused even more damage.
- I had to scramble to install additional security cameras and replace the broken windows.
This was a huge headache, but the story doesn’t end there.
The day after the second round of vandalism, I got a booking request—a workgroup wanted to rent the property for the entire month of February.
The only issue? They wanted to check in just two days later.
I explained what had happened and told them we’d have the house ready (except for the graffiti cleanup).
They were fine with it, so we went into overdrive to get everything repaired in time.
Was it stressful? Absolutely. But the $4,200 Airbnb payout made the effort worth it.
Why Conviction Matters
These stories aren’t outliers. They’re part of the reality of real estate investing. If you don’t have a strong vision for why you’re investing, challenges like these can break you.
Here’s what I’ve learned:
- Real estate is far from passive. No matter how well you plan, unexpected issues will come up.
- You need to be financially prepared. Emergencies, vacancies, and rehab surprises happen. If you don’t have the capital to weather them, you’ll struggle.
- Time is your friend. Bad deals can turn into great ones with enough time, patience, and solid management.
- Your mindset determines your success. If you go into real estate investing expecting smooth sailing, you’ll be disappointed. If you expect challenges and commit to overcoming them, you’ll build a solid, long-term portfolio.
Wrapping It Up
Real estate investing isn’t for the faint of heart. It’s not a get-rich-quick scheme, and it’s not as easy as some books and YouTube videos make it seem.
But if you have strong conviction, a clear strategy, and the resilience to push through when things get tough, it can be incredibly rewarding.
Challenges will come—but how you handle them determines whether you succeed or quit.
So ask yourself: Do you have what it takes to stick with it when things go sideways?
Because that’s what separates real estate investors from those who just dabble.