Young Money: How one 25-year-old left Toronto and became an accidental landlord in Windsor

Young Money is our five-part series this week chronicling young Canadians and the lessons they learned making big financial decisions. Click here for a recap of the entire series.

Name: Rob Benneian
Age: 27
Where: Windsor, Ont.
What he does: Real estate agent

After six months in Toronto, Rob Benneian​ began to wonder if he could pay rent, much less buy a house.

It was 2014 and Rob was a recent journalism grad. He was making $15 an hour, working part-time at a sports radio station and could barely afford his $1,000 rent in a shared three-bedroom Scarborough apartment.

So he decided to move home to Windsor. 

Within a year, Rob had a steady job in his field, bought a detached home and became an accidental landlord (more on that later).

All he had to do was drive four hours southwest of Toronto.

For lots of young professionals in Canada, carrying a mortgage is actually cheaper than renting, and downpayments are nowhere near as daunting as they are in Toronto or Vancouver. So the great Canadian dream of homeownership is very much alive and well — and lots of young people are taking full advantage.

Here’s the story of how one millennial bought a detached home two years ago at the ripe age of 25.

Bloom where you’re planted

Rob Bennenian was born and raised in Windsor, but after graduating from St Clair College with a post-secondary diploma in journalism, he — like so many others from the area — headed for the bright lights of Toronto in search of a career.

What he found was less than promising.

"I got my foot in the door at TSN 1050, which was exciting, but it wasn’t a permanent role," he says. "I liked the city, but living costs were insane. I couldn’t afford to wait around until I found something full-time."

After trying to make it work for six months in the big smoke, Rob found an elusive sports marketing gig in Windsor and decided to pack up and head home.

I liked the city, but living costs were insane. I couldn't afford to wait around until I found something full-time

Once known almost exclusively as a manufacturing town, Windsor has recently been diversifying its reputation as a means of attracting and retaining young people like Rob. While job opportunities are obviously fewer than in larger cities, the region is rebranding itself as an entrepreneurial-friendly tech hub that boasts a growing but still affordable housing market — with average prices hovering around $220,000.

The perfect combination of career and lifestyle that many millennials look for when choosing a city.

"A lot of people dump on Windsor, but I’ve got love for my city,” says Rob. “It’s not for everybody, maybe, but it’s got character and it’s affordable."

If you can, lean on your family

Getting into the housing market can be confusing, overwhelming, and riddled with unexpected costs. So how did Rob manage to navigate the process as a first time homebuyer? He leveraged the support and expertise of his family.

Luckily for him, his dad is a real estate agent in the area, so he was able to gain valuable insight into the local housing market and the purchasing process. There’s nothing like family support when you’re going through one of life’s biggest financial decisions, and that’s exactly what Rob enjoyed when he moved back home.

"Honestly, I was pretty intimidated to buy a house,” he says. “I had just moved home, just started a new job, and had no idea what to look for."

Honestly, I was pretty intimidated to buy a house. I ... had no idea what to look for

With professional advice he could trust, and with a steady job that — while not the most lucrative — paid enough to buy in one of Canada’s best cities for jobs and affordable homes, Rob decided to take the plunge.

Find your happy place

Rob looked at more than 20 places before settling on a detached, multi-unit dwelling in the uber-affordable east end of the city, near the historic Ford City neighbourhood. Once a thriving hub for workers from the nearby Ford auto plant, the neighbourhood has since fallen on hard times, putting it well within the reach of young buyers.

The house was listed at $125,000, and that’s the exact amount he paid. Nary a bidding war in sight.

This meant that Rob only needed to put down $6,250 (meeting the 5% minimum down payment), which was easy with a bit of help from his folks. Monthly mortgage payments worked out to just over $700 — even in Windsor, you can’t rent a full house for that. So all in all, pretty manageable numbers, even for a recent grad earning an entry level salary.

The accidental landlord

There was another factor that contributed to the financial feasibility of buying the home: it came with a paying tenant.

"I’m not the most handy guy and really knew nothing about being a landlord, but getting a tenant made so much sense," Rob says. "I wasn’t killing it in terms of salary, so the rental income was huge in terms of affording the payments."

The tenant had been living in a separated part of the home under the previous owners. Rob had no experience managing a rental property, but after meeting the tenant and doing some thinking, he agreed to take on the mantle of landlord.

The house was listed at $125,000, and that’s the exact amount he paid. Nary a bidding war in sight

Fast forward two years and Rob’s mortgage is down to $110,000 — about the same amount many homeseekers in Toronto are trying to save for just the down payment.

And wouldn’t you know it — Rob’s journey from barely scraping by on rent to collecting it has also pushed him into a new career. He's now selling homes in the Windsor area. You can check out his real estate profile, or hit him up on Twitter.