This story began almost two years ago when my first long-term tenant moved out. I listed the unit again through my trusted realtor, and by God’s grace, my very first tenancy had been an absolute blessing.
That tenant came through a company that sponsors refugees from war-torn countries. Not only did they secure housing and provide employment for newcomers, but they also ensured rent was always paid on time and even handled minor repairs themselves. It was truly a hassle-free, joyful two-year experience as a landlord.
But my next tenant? That was the turning point—and the reason I will never again be a traditional landlord in Ontario.
On paper, the tenant looked fine: decent credit score, professional job in Windsor, and part of the rent paid directly by the government. I thought it was a safe bet. Instead, it became one of my worst nightmares.
Rent payments came late more than once, but the real issue was the daily complaints and emotional drain. I felt less like a landlord and more like a full-time counselor. To make matters worse, she brought in three dogs and three toddlers. The unit quickly deteriorated into a garbage dump.
Over their 10-month stay, I received constant complaints from upstairs guests (who shared the same air vents) and even from contractors. One of my cleaners—who had been in the business for over a decade—said it was the worst home she had ever encountered. Another vowed never to do residential cleaning again after two grueling days in the unit.
By the time I regained possession, the place was unrecognizable. But instead of giving up, I decided to turn the disaster into an opportunity. After three months of renovations, I transformed the unit into a stylish, fully functional Airbnb—and the results have been beyond rewarding.
Renovation
With a limited budget, I had to prioritize carefully. The kitchen became my top investment, and it turned out to be the best decision I made. Guests often choose Airbnb over hotels for the ability to cook, especially families. A beautiful, modern kitchen would be a key selling point.
Since my kitchen is relatively small, the remodel was affordable. For under $8,000, I installed granite countertops and a brand-new Frigidaire stainless-steel stove. Paired with fresh paint and deep-cleaned floors, the transformation was dramatic. Guests often tell me they can’t even recognize the unit anymore.
Furnishing
After five years in the Airbnb business, I’ve learned that photos make or break your listing—and great photos depend on thoughtful furnishing. You don’t have to overspend, but you do need to be strategic. With time, creativity, and smart shopping, I furnished the two-bedroom unit stylishly for under $10,000.
I’ve even built a workflow to streamline the process. For those in Windsor looking to set up their first Airbnb, I now offer both consulting packages and full set-up services to save you the guesswork.
Airbnb Listing Strategy
Once your photos shine, the next battle is visibility. A strong, SEO-friendly listing helps get you on the first pages. But the most important factor is mindset: treat hosting as continuous improvement.
For my first few guests, I asked for honest feedback at checkout. One guest mentioned a lingering smell and the firmness of the mattresses. Instead of leaving a bad review, she kindly shared her input—and I not only made immediate changes but also gave her 10% off her next stay as thanks. That kind of relationship-building pays off.
Outcome
Within the first month of relaunching as a two-bedroom Airbnb, the unit was booked 90% of the time over the following three months, generating around $3,000 per month. This far exceeded my expectations, especially during a market slowdown.
The success confirmed what I’ve always believed: the right renovations, smart furnishing, and thoughtful hosting strategy can turn even the worst property into a thriving short-term rental.
What’s Next
Today, out of passion and experience, I run CoHostsCircle, an Airbnb management and mentorship company. We help investors and homeowners launch successful short-term rentals with confidence. Unlike traditional property management, we combine hands-on services with education to set you up for long-term success.
If you’ve ever thought about starting your Airbnb journey, now is the time. Don’t hesitate—start today.