Ah, real estate—the land of passive income and endless opportunity, right? Wrong. For me, it turned out to be a wild roller coaster ride through the land of unpaid rent, escalating drama, and threats worthy of a daytime soap opera. But like every North American underdog story, there’s a silver lining—I emerged victorious, clutching the keys to my new best friend: Airbnb. Here’s my tale of woe, sprinkled with lessons, some laughs, and a truckload of drama.
The Condo of Dreams… and Nightmares
Once upon a time, I was the proud owner of a lovely 1+1 condo in Richmond Hill, Ontario. It was cute, cozy, and full of potential—kind of like the starter home version of your first love. I envisioned steady rent, stable tenants, and a future where my dad could retire in a place where the neighbors all spoke his language.
But oh, the universe had other plans. During the six years I owned the property, I had three tenants. Two of them made me question my life choices, and one of them? Well, let’s just say he gave Freddy Krueger a run for his money when it came to nightmares.
This particular gem managed to stay rent-free for 10 months while hurling verbal and physical threats at my realtor, my boyfriend, and yours truly. It was like living in a Netflix drama, except I wasn’t being paid to star in it.
Tenant Screening: A Comedy of Errors
Now, before you roll your eyes and blame me for not screening properly, let me tell you—I did my homework. My trusty realtor helped me scout for “AAA tenants,” which, in real estate lingo, basically means “tenants who won’t ruin your life.”
One application stood out: a gentleman with an 800+ credit score (cue applause), an almost six-figure income, and a job as a Senior Associate at his mom’s dry-cleaning business. Bonus points? He was married, expecting a baby, and had glowing reviews from my realtor, who met him in person. I thought I’d hit the tenant jackpot.
Spoiler alert: I didn’t.
The Red Flags I Ignored Like a True Optimist
The warning signs came early, but I, being the eternal optimist (or naïve landlord, take your pick), ignored them.
First flag: He called before the second month’s rent was due, asking to pay via e-transfer instead of post-dated checks. “No problem,” I said, trying to be the cool landlord. Then he added, “Oh, and the rent might be a couple of days late.” Hmm. Red flag? Maybe. But hey, life happens, right?
Second flag: He started grumbling about the storage locker. First, he didn’t need it. Then, suddenly, it was a dealbreaker. What followed was a circus act of me emptying out the locker, coordinating with my realtor, and playing mediator between him and his wife. All for the rent to arrive two weeks late.
Third flag: By month four, I was sending daily texts begging for a few hundred bucks here and there. He apologized at first, blaming the dry-cleaning business, his family responsibilities, and probably the alignment of the stars. But eventually, he stopped answering my calls altogether, vanishing like Houdini.
When Things Got Ugly (Like, Jerry Springer Ugly)
By month six, the gloves came off. I filed an N4 (a legal notice to evict) with the Landlord and Tenant Board (LTB), thinking I’d finally have some leverage. Nope. Filing paperwork with the LTB is about as effective as trying to fix a broken sink with duct tape—it’s messy and ultimately useless.
The tenant didn’t take kindly to my eviction attempts. When I arranged an in-person meeting with him (and brought backup: my boyfriend and a third-party realtor), things got heated. He taunted us, threatened physical violence, and made me wonder if I should have brought a referee instead. We ended up filing a police report.
The Bitter End
After 10 months of unpaid rent and countless headaches, I waved the white flag. I decided to sell the condo, even though it meant giving up my dad’s dream retirement spot. Luckily, the tenant’s realtor managed to sweet-talk him into leaving, and I sold the property at a decent price.
The LTB ruled in my favor (yay?), but with no assets to garnish and no enforceable means to recover the rent, it felt like winning Monopoly with fake money.
Enter: Airbnb, My Knight in Shining Armor
Once the dust settled, I took a hard look at my real estate portfolio and decided I’d had enough of long-term tenants. Life is too short to chase rent payments and dodge threats. So, I pivoted to Airbnb, and let me tell you—it’s been a game-changer.
With short-term rentals, I have control. Guests come and go, payments are upfront, and if someone even thinks about misbehaving, I have the power to hit that cancellation button like a judge with a gavel. Plus, I get to decorate my properties like HGTV exploded in them, and guests actually appreciate it.
Happily Ever After
Three years later, I’ve never been happier. My properties are thriving, my guests leave glowing reviews, and I’ve all but forgotten the horror of those tenant-filled days. Okay, maybe not forgotten, but at least now I can laugh about it.
To anyone considering real estate: If you’re up for a soap opera, go ahead and lease long-term. But if you prefer peace, quiet, and a steady income stream, Airbnb might just be your new best friend. As for me? I’m living proof that happiness really is priceless—and sometimes, it’s just one Airbnb booking away.
A New Mission: CoHostsCircle
After transforming my own real estate portfolio into a thriving Airbnb operation, I realized something: I’m not alone in this struggle. There are countless landlords out there dealing with late rent payments, endless headaches, and tenants who seem to think eviction is just a game of hide-and-seek.
So, I decided to do something about it. I started CoHostsCircle, an Airbnb property management company dedicated to helping property owners like you escape tenant drama and embrace the freedom of short-term rentals.
With CoHostsCircle, I take the stress out of hosting—handling everything from guest communications to property maintenance—so you can sit back, relax, and enjoy the steady income. Think of me as your personal Airbnb fairy godmother (minus the wand, but with way more spreadsheets).
Curious? Head over to www.cohostscircle.com or schedule a free consultation with me. I’d love to share my story, answer your questions, and help you turn your properties into stress-free income generators. Because if I can do it, so can you.
