Real Estate Market Opportunities for Ontario Landlords in 2025

Hey everybody, welcome to another episode of the Ontario Landlord Series presented by CRESI. Today we’re going to have a conversation with Gary Hibbert. He’s a realtor and investor specialist from the east end of the city out in Peterborough. He’s been working at his brokerage — I’ve been seeing Smart Home Choice around for close to a decade now — and we’ve gotten to know each other a bit over on that side of the city.

We connected a little bit, and we’re going to bring him on today to talk to you about it. I’ll let him introduce himself better than I can. Here we go — this is Mr.

Gary Hibbert. How are you doing today? I’m great, man — thank you very much for having me here, Kevin. Excited to do this, and to share what I’ve learned over the years — not just the successes, but I think more importantly, the mistakes. I want people to learn from the mistakes I’ve made so they don’t have to step on the same landmines.

That’s amazing — I was just speaking with a client today who sadly bought something without us, had a great idea but a very poor plan and a poor team around her, and now we’re trying to dig back and correct the issue that got created. So I agree with you 100% — passing down the wisdom of past mistakes is a great way to help people avoid making those same mistakes.

Why don’t you start off and give us a little description of yourself — who you are, what you do, and how you help landlords. Geez, how do I help landlords? Look, I’m a real estate investor.

I’m a real estate agent. I started investing back in 2008. The reason I got into it was because I realized I couldn’t outpace inflation. Inflation was only about 2% back then.

And my raise at work was less than 2%. The one thing that had bailed me out several times was my house, so I thought, what if I just bought one more? That led me down a path of going to real estate investing rooms and learning from people who were where I wanted to be.

From there, I started a company called Smart Home Choice, a real estate education company. The funny thing is, I didn’t know much about real estate investing at first — I made a couple of mistakes in the beginning. I only had two or three properties at that time.

What I did was reach out to people who were successful, industry experts, and had them come in and talk to our very small group of investors at the time — friends and family, and whoever wanted to come out and learn a bit more about real estate investing. That helped me build my network. Fast forward, we’ve been doing this now for 15 years, we’ve got a great network of industry experts, and we’ve invested anywhere from Toronto to Durham Region to Peterborough,

along the 401 corridor, and I continue doing it. I love it, and I love giving back to the community. My whole philosophy is that just one investment property can change your life — you don’t always need a thousand doors, but one or two can make a big difference, especially in the world we live in today with so much inflation. A lot of investors don’t want a bunch of properties.

They just want that one property to help with retirement, or whatever they’re thinking of as a savings plan. But what those landlords don’t always realize is that it’s still a business — they’re still a landlord, and they have to do things properly.

You can’t just think “my house appreciated, that house will appreciate too, and down the road I’ll cash in.” There’s a lot that happens along the way — a lot of tax breaks and other things landlords, as business owners, can take advantage of that a lot of people miss out on. I like what you said about the education piece.

That’s something we always try to do as well — educate and inform so people can make whatever decision is best for them. We’re as individual as our fingerprints — what some people want, others don’t — but information is something everybody looks for. Exactly.

And there are so many different investing strategies out there. One of the best things to do when you first get into it — there are a lot more real estate investment clubs today than when I first started, there were very few, and I had to travel to Oakville or Mississauga to learn. But here’s what you should do for the first three to four months: attend events, hear a bunch of different real estate investing strategies, and it shouldn’t take more than four months or so to pick a strategy that suits your lifestyle and run with it.

And don’t worry about any other strategy — just pick that one, focus on it, and I’d say stick with it for at least three or four years before deciding to move on to something different. Master one before moving on, right?

You can’t really be a jack of all trades. Right — no, that’s excellent. You mentioned your investing group and everything that goes on there.

I’m sure you’re hosting events. Do you have one coming up you want to talk about? Yeah. Oh man, I’ve got an awesome event happening.

It’s on May 8th, out in Ajax at the Ajax Hilton Hotel. I’ve got over 10 or 11 speakers coming out. I’ve got a woman who analyzes faces — she’ll be analyzing Robert Kiyosaki, Grant Cardone, Donald Trump, looking at their eyes, eyebrows, nose — kind of a fun way to warm up the crowd. Then I’ve got a speaker who was part of a rain-water panel talking about investing in garden suites out in Peterborough.

They can actually now do four units out there, so we’ll touch on that. Then I’ve got a panel discussion on infinite banking. My mortgage agent will be there too, talking about whether you should break your mortgage, lock in, or what’s happening in the market. I’ve also got a speaker who’s going to talk about the art of the deal.

And what else — Alfonso Cuadra will be there as the keynote speaker. The way we’re going to do it is Alfonso and I will be up front just having a conversation.

We’re going to let the crowd ask us questions. I’ve got my lawyer there talking about what’s happening in the condo market, and Rent Panda will be there to talk about where things stand in the rental market right now. I’ve got a couple other speakers too.

I can’t remember them all, but it’s going to be a packed night — super excited for it. If people want to register, that’d be great, and thanks for letting me share that.

Everybody, the link will be in the comments or the bio wherever it ends up being placed — if you can’t find it, reach out to me and I’ll make sure you get the link so you can register for the Mastermind event on May 8th. With everything going on right now — you mentioned garden suites, and I think that’s huge given the densification happening in different municipalities, everybody wants a bit more space. Garden suites are a very interesting topic — people are thinking about how it’s going to affect their lives.

I think that’ll be a good session. I’m getting questions about garden suites all the time. There’s a company out in Guelph I’ve started to look into that’s building them — there aren’t a lot of options for people to do that right now.

There’s really just a little bit, because it’s still so new to everybody. But I think it’s a great way to add income to an investment property. I don’t know that I’d want anybody living in my own personal backyard, like some people do, to supplement income — but if you have a duplex, putting one out back is a great way to add a bit more income.

For sure. And I’ve worked with a lot of first-time home buyers as well, outside of real estate investors, and for some of the clients I’ve worked with looking for their very first home — it’s not cheap anymore. That mortgage can run anywhere from $3,000 to $4,500 to $5,000 a month.

If you can supplement your income by converting the basement into a second unit, or by buying a turnkey property, you can potentially cut your mortgage payments in half. When you start getting into a garden suite, whether you’re an investor or just a homeowner, that’s a great way to get started — but you don’t have to jump right into the garden suite right away.

Then when you move to your next home, you do the same thing again — I’ve seen clients do that. By their third home, because your first home shouldn’t be your dream home, that third home can become your dream home.

And then you can start adding garden suites to those properties, because it’s not cheap to add one either — but you want to look for properties that allow for it. So really what I’m saying is this opens up to not just investors but homeowners too. We talk a lot about basement apartments — that’s also a really hot topic right now.

We’ve actually strung together four episodes about that, which we’re going to package into one video — a bit of a plug there. It covers different professionals: the contractor, the mortgage agent, the insurance broker, and the paralegal, just so people understand — because even if you’re living upstairs and renting out your basement, you’re still a landlord.

Even though you live on the property, you’re still a landlord — the RTA is in effect, and the LTB is what governs everything. You need to understand what’s going on while a tenant is living in your basement. There’s a great way we come in for a couple of our clients who live upstairs and rent out their basement — the basement tenant might believe the person upstairs is also a tenant, so those clients use our management services so they don’t have to be the one who gets bothered on a Saturday night. That’s a great feature — the owner can just say, “let’s call CRESI Property Management, don’t worry, we’ll get it fixed,”

whether it’s the owner or the tenant calling us. They’re both effectively treated like tenants in that dynamic, and I think it’s a great way to give the owner some peace while living upstairs, because it’s still two completely separate units. Yeah, look — especially if you’re doing this for the first time, I think the most important thing is to lean on the experts.

Have somebody — whether it’s a property manager, a home inspector, or a contractor — always reach out to experts and lean on your network. It makes things so much easier, especially today, when you want to make sure you’re putting the right person in your property, particularly if you’re living there yourself. The most important thing is tenant screening — putting the right person in, because once they’re in, they’re in. The only exception is if you’re sharing a kitchen or something similar.

If they’re in a completely separate dwelling, the same rules apply as if they were renting a separate condo you own. Definitely make sure you know who you’re using, whether it’s your realtor doing the screening or other screening tools out there. I agree with Gary 100% — always use professionals for everything.

It’s the best way to go. Things are getting more sophisticated — there’s AI, there’s documentation fraud, so many different things people can try. If you’re not familiar with the right questions to ask or the right documentation to check, it doesn’t take much for a bad tenant to slip through. And if you are going to do it yourself, be careful of people tugging at your heartstrings.

You always want to see all the documentation, because professional tenants are really good at blending in with the rest of the crowd. I’ll share an interesting stat — I talked about this when I first got into investing, and I asked someone recently if the numbers are still similar: about 80% of tenants are good, 10% are great, and 10% are bad. The numbers may have shifted slightly, but the bottom line is that 10-15% of tenants who are bad, or who are professional bad-tenant types, are really good at hiding among the other 80-90% who are good. But that stat also shows you still have a very high success rate. The problem is what’s highlighted on the news and social media — that all tenants are bad.

Yes, there are some bad apples, 100%, but the overall success rate for most people who just want a place to live is high. If you educate yourself properly and understand how to protect yourself from the people who are bad, you’ll see the same in any industry — the success rate is very high. My own portfolio is close to 100% good tenants across the properties I own. It wasn’t like that in the beginning — I learned a lot early on — but if you’re not sure what you’re doing, make sure you’re reaching out to people who understand it.

The number is actually close to 40% of Canadians who rent. So you can’t say that all 40% of Canadians are bad apples. And at the same time, there are bad landlords too — I truly believe sometimes bad situations create bad tenants and bad landlords when something isn’t dealt with properly.

Having a property manager or somebody in the middle to communicate back and forth, instead of it getting emotional between two people, is a great way to handle things when something needs fixing or two sides don’t see eye to eye. But a lot of tenants are very good people — if everything was perfect for that tenant, they’d probably have bought a house already.

There’s a reason they’re renting — it’s always a piece of the puzzle. If someone says they have bad credit, I want to know why. Maybe they’re going through a divorce, or coming out of something difficult — we can work through different things and understand the situation. Credit is definitely something to look at and understand the reason behind, but

it’s not the be-all and end-all when you’re evaluating someone. Exactly. So our market right now — you’re on the east side, I’m on the west side, but I don’t think it matters, I think it’s the same across the country. Real estate is on sale right now — there’s a lot of condo inventory, assignments, new builds coming out, resales that have been around a while, and prices are much lower than before, 25 to 30% off the peak in some cases. These are deals to be had. This is definitely a time to buy, right?

Don’t you agree? 100%. I think right now there’s a lot of fear in the market. The numbers are finally starting to make sense again — interest rates are coming down. There’s some concern about tariffs and where things are going, but

I do believe we’re going through a very large transfer of wealth, and unfortunately there are winners and losers — so there are properties right now where you can get real deals. But you’re also creating a win-win, because sometimes you’re getting somebody out of a situation they no longer want to be in, and there are some great opportunities right now. What you have to do when you’re looking at these opportunities is make sure — and I’ve said this from the beginning, learned it early on — it does cash flow. Is this something that can cash flow?

That’s number one. Number two — does it have a higher and best use? The problem with condos, which I never got into, is that it was a very speculative game for so many people — like going to the casino and gambling. For many years it was a great gamble.

Unfortunately, when it turns, it can wipe you out completely, and that’s what you’re seeing right now in the condo market. Will it come back? Of course.

Do I think if you’re looking to get into the market now it’s a good time to buy a condo for personal use? Possibly. Eventually you may want to raise a family, but it’s a way to get into the market if that’s what you can afford.

There are lots of great opportunities out there right now. I haven’t bought anything since 2019 domestically — I bought outside the country — but I’m now looking to pick something up, possibly in Toronto, because with the change in bylaws, you can now turn a single-family home into a four- or five-unit property. That now makes sense.

The numbers make sense, and that’s what I’m always looking for — cash flow, higher and best use, and what I can do with the property. I think it’s a phenomenal opportunity right now. A lot of people don’t talk about this, but during the Great Depression,

you hear about the depression part and how many people were unfortunately on the wrong side, but during that time was also when some of the most wealth was created. That’s where families like the Kennedys got their money.

Same thing in 2008 — wealth doesn’t just disappear, it transfers hands. There were losers and there were winners in 2008 too.

And you’ll see the same thing in this market — you just have to be on the right side of it. Sadly, some people got stuck in the condo market. I think what happened was too many people started to think real estate was a get-rich-quick scheme rather than a get-wealthy-slow one.

Assignments were going crazy in the mid-2010s, with people making $100,000-plus off paper just from assigning contracts over a couple of years, and all that speculation led to people overpaying. I read the other day the Toronto condo market bust is expected to cost investors somewhere between $10 and $14 billion, which blows my mind. I’ve spoken to people who bought more than they can handle and can’t close now, and they’re trying to figure out different ways forward. It’s unfortunate, but I think it came from having a poor plan, in my opinion, because you never know what the future holds — but as Warren Buffett says, when others are greedy, you should be fearful,

and when others are fearful, you should be greedy. Right now people are definitely fearful — “uncertain” is the word I hear all the time. I don’t know what’s going to happen. One thing I do know for certain is that every Canadian needs a roof over their head.

Whether you own it or rent it, you still need that roof. So it’s a good time for investors to be picking up another property. Let’s talk a bit about conversions, because I agree with you there too — taking something and converting it to a higher and best use is definitely a way to increase your ROI, however you’re doing that.

Whether it’s turning a big one-bedroom into two beds, or cutting up a house into a triplex or fourplex, involving contractors and getting permits in place — I wanted to talk a little about your process there. When you’re talking about conversions, you’re creating multiple units, and what you’re doing is force-appreciating that home.

There are different ways of doing it, and different markets you can do it in. I think Toronto is a great opportunity right now, but you do need deeper pockets — no doubt about it.

You’re looking at an entry point of maybe eight hundred thousand to a million dollars for a decent neighbourhood you could turn into four or five units. If you want another conversion market, an area I really like is Peterborough — coming up soon, you’ll be able to go up to four units out there.

The entry point there is anywhere from the high $400,000s — you can get into a decent neighbourhood in the mid $500,000s. That’s an easier price to digest, and you can easily convert it into a two- or three-unit — I believe the main house can now do three units plus a garden suite in the back.

I’ll share this with you too — at the peak of the market, in 2022, one of my clients bought at the peak in Peterborough and converted the property into a two-unit. They don’t have a garden suite yet, but they have the lot size for one. And they’re cash-flowing over $1,000 a month.

That shows that even when you buy at the highest or lowest point of the market, the numbers can still make sense as an investor. I think a lot of people forgot fundamentals, or maybe they never understood them — that’s one reason I like conversions. I like the forced appreciation and the higher and best use.

I’ll wrap it up by saying that when you’re looking at a market, whether it’s Peterborough or wherever, look at the fundamentals. Is the population going up? Are jobs increasing?

Is infrastructure being built in that area? And “eds and meds” — education and hospitals. Take a look at some of those fundamentals to see whether a city makes sense. I love secondary and tertiary markets.

It makes sense to me. Some people say, “well, I wouldn’t live there,” but you don’t have to. You’re renting it out.

The investor never lives in the property — I had a couple from Oakville buy something in Hamilton, and that’s exactly what they said to me. I would never live here, they said, and I told them there are plenty of people who would. You just have to get over the fact that it doesn’t have to fit your own needs — it’ll work for a lot of different people. We go through that with clients all the time to make sure they understand. Exactly — as you mentioned with fundamentals, it’s location, location, location, right?

That’s the one thing that doesn’t change. It’s the one thing we always say, and it matters most — I think even more than when you’re choosing where to live, it matters more when you’re choosing an investment. One of my little tricks when I’m thinking about areas — I don’t have millions of dollars to spend on research and development — but I do know that Shoppers Drug Mart and Starbucks do that kind of research. The areas they’re in tend to be more affluent, so it’s a sign you can use to figure out location. You’re also looking at transportation, because a lot of tenants use public transportation, whether it’s GO Train or subway.

100% right. Transportation is very important. One of the reasons we ended up going to Peterborough was watching the 407 develop, before it connected to the 115 highway — we saw where it was going and what was happening in the future plan.

So you also want to look at where the future plans are — where is that GO Train line going, where’s the LRT or subway going? Once you start looking at those things, you start making educated, calculated decisions, but always remembering cash flow.

It’s not a difficult game, but you have to realize it’s not a get-rich-quick game. You never know when appreciation is going to come, so don’t count on it. The last couple of years showed exactly why not, right?

You focus on cash flow. Cash flow is incredibly important. I agree with that. Value really only matters with your property when you’re buying it, selling it, or refinancing it.

At the end of the day, if you bought a property for half a million dollars, and your rent covers your mortgage, then as long as those payments stay the same, the property’s value dropping doesn’t change your day-to-day cash flow unless you’re buying, selling, or refinancing. Making sure you have money coming in is great — that’s why we also like multiple units, because with a single-family home, if that one tenant can no longer pay, you have zero income coming in for the property, whereas with multiple units, you at least have some cash flow to keep things going. Agreed.

Life happens, right? I had a tenant have a stroke once — you have to go through different things to get him back on track, but things happen, and you just have to figure it out as you go.

I think this has been a great conversation, and I hope people got something out of it. Before we let you go, I’m going to ask for your biggest or best landlord win you want to share. I’ve had a lot of wins,

and I’ve had a lot of losses too. The biggest one — maybe this is an interesting one — back in 2016, my partner and I bought an investment property in Oshawa. We picked it up for around $250,000-something, a detached home, and we converted it into a two-unit. We finished the upstairs first and put a tenant in.

The rent from that upstairs unit covered the mortgage payments, so we were essentially breaking even, which was perfect. Then we went to the basement and started that conversion — we had to waterproof the basement because water was coming in. We did a property tour to show people what we were doing, and that was actually the start of doing property tours. When people saw what we were doing,

they wanted to do the same thing. At the time I don’t even think it was called BRRRR yet — we were just going in and renovating it. Then we put tenants in the basement.

We ended up extending the length of time it took to complete, because it was basically break-even anyway, and as realtors we were getting transactions out of that process too. We did that for about a year and a half — felt like two years, felt like forever. That was a huge win for us, and it’s where we showed a lot of people how to do the BRRRR strategy and single-family-to-two-unit conversions. If you’re not familiar with the BRRRR strategy, it’s buy, renovate, rent out, refinance.

With that, you should be able to pull out some tax-free money that you can either put in your pocket or reinvest into another property. It’s a very good strategy, and we’ll get into more detail on that in another episode. That’s going to bring today’s episode to a close.

Thanks, everybody, for listening. Gary, thanks so much for joining and sharing with us today. Thanks so much for having me — I appreciate it.

I always enjoy doing this, sharing my knowledge and my journey, and the mistakes I’ve made along the way — even if it only reaches one person and they’re able to take something from this conversation, then it did exactly what it was supposed to do. Don’t forget about the Mastermind on May 8th — if anybody wants to go, I’ll be going too, so we can ride up together from the west side to the east side and have a good day learning from an awesome panel of speakers. As always, thanks so much for listening.

If you know a landlord out there who needs great information like this, please pass along this podcast to them so they can get the same information we’re sharing. As always, thanks so much for listening, and we’ll see you again soon. Bye. Please remember, while we are professionals, this podcast is for informational and entertainment purposes only.

The advice shared may not apply to your unique situation. Always seek personalized advice from a qualified professional before making any investment decisions. Hey everybody, thanks so much for joining us this week. I hope you enjoyed the episode.

If you’re finding it informative and useful, make sure to like, subscribe, share with a friend so that we can keep getting the information out there to Ontario landlords. Keep on joining us — we’ll see you next time.