If you’re thinking about becoming a landlord in Canada… or you just signed your first rental… I want to share how I lost $35,000 as a beginner landlord. And what it taught me to do differently.

I’ve been sharing this with thousands of other landlords in hopes they don’t also make these mistakes I did. And I hope this helps you avoid the same mistakes to

So. Flash back to when I was 23, I bought my first place. I was pumped, I was proud, and I thought I was building wealth. Hooray.

But I didn’t realize I was also stepping into a massive, regulated legal machine that I barely understood. A few months later, my tenants just decided to stop paying me. So the rent checks just stopped. By the time I finally got through it, I’d lost over $35,000 in unpaid rent and legal fees.

And that really sucked, but besides the money, the stress was actually worse. Like, endless court hearings and stacks of paperwork. I felt totally stuck because the system was dragging its feet while my mortgage payments were still very much due every single month. So today, I want to talk about what I wish I knew back then. Because even after all that… this was still one of the best moves I ever made for my family. You just have to know how the game is actually played.

You play by new rules now

When you get that first rental, you feel like it’s this exciting real estate play. But once you’re in it, you realize you’re now responsible for things like the Residential Tenancies Act. And you’re answering to the Landlord and Tenant Board now. Your life becomes all about deadlines and specific forms.

Everyone talks about how being a landlord is supposedly "passive income"—but in reality it's a full-time job staying compliant with a whole host of regulations. For example: if someone stops paying you rent, you can’t just shoot them a text. You have to serve a very specific document - known as an N4. And that document is super picky. It needs the exact rent arrears, the perfect postal code, and the termination date has to be calculated down to the day. If you mess up the count or put a utility bill on there that shouldn't be there? The whole thing gets tossed. The board doesn't care if you're a "nice person." They care if the paperwork is perfect. It’s things like this that can really screw you over if you aren’t educated on your responsibilities as a landlord. In fact, that exact example was my first big wake-up call.

Dealing with Non-Payment

Next: Dealing with Non-Payments.

When my tenants stopped paying, I'll be honest—I took it personally. I felt like I was being targeted. But I had to realize that non-payment is just a part of the math of the business. It’s a risk model, not a personal vendetta. If you’re in the housing business, you have to expect that at some point, someone is going to stop paying or try to fight the system. Your job isn't to get angry or panic; but to calmly move through the steps: N4, then L1, then the hearing. If you treat it like a standard operating procedure instead of a personal battle, your stress levels will drop significantly.

By the way, lot of landlords don't know what to actually expect at that hearing. It sounds complicated but a hearing isn’t like what you see in a courtroom drama. It's usually more like a short session with a Board member where both sides get to present their case. You'll show your paperwork, the tenant gets to respond, and the member makes a decision. It's usually quite anticlimactic. If your documentation is solid, it's often pretty straightforward.

Then when you win, you walk away with a piece of paper called a court order. Which doesn’t seem like much, or honestly do much… But as I’ll share in a moment, we’ve actually built a powerful tool around that piece of paper. To help landlords all across Canada share their court orders and make them searchable so landlords finally have a way to help each other as a community and see if a potential client has any past court orders against them. I won’t get into it too much just yet, but it’s called Openroom.ca and if you’re interested I’ll share more in a bit.

Winning is Only Half the Battle

Next - Winning isn't always "Winning."

I remember thinking that once I finally "won" at the Board, that was it. I thought the money would just magically appear in my account. I was so wrong, and honestly, it’s a huge letdown when you realize that winning a judgment is really just the start of a whole new headache.

Collecting that cash is a completely different project. Like, if your tenants decide they just aren't going to pay you voluntarily, you’re forced to file for debtor exams, hunt down where they work, and try to garnish their wages. It’s basically a second job. I’m telling you this because nobody prepares you for the fact that the system is incredibly slow.

And just to give you a taste of how slow it really is…

Month 1, Day 1 rent is due. Month 1, Day 2 you can issue an N4 notice. Month 1, Day 2 + 14 days you can file the L1 to get a hearing. +3 months to get a hearing date. +unknown months for potential adjournment, stays/appeals. +2 weeks before you can even book a sheriff. +several weeks before a Sheriff date is confirmed with you. +1 to 6 years to wait for an actual repayment of your debt, if you’re lucky to get anything back.

So if you don't have your ducks in a row from day one, getting paid back becomes ten times harder and it can really screw you over financially. Your goal here really should be “how do I not get into this situation to begin with?”

Paperwork is Everything

Something else I learned: Paperwork is everything.

I used to think that being the "easy-going landlord" would make things smoother. It didn't. It actually made things worse. I tell every landlord I work with now: you have to be a professional. And being a professional means you document absolutely everything.

I mean everything—your rent ledgers, every single email, and even screenshots of your texts. When you eventually walk into a hearing, you aren’t there to tell a sad story about how you feel. You are there to present a file. The board member doesn't care who feels more "wronged" in their heart; they’re just looking at the receipts. Seriously I can’t emphasize this enough - you need to get in the habit of collecting solid documentation.

If you end up at a hearing, you're going to need to prep an evidence package with organized timelines, clear records, and everything laid out so the Board member can follow it clearly. The mentality you want to adopt is "don't make me think." That's what a judge or Board member is thinking when they're sitting across from you. They want a clean, easy-to-follow file.

If you don't show up with that, you're either paying a lawyer to organize it for you, or you're getting sent back to do it properly anyway. Either way, it costs you. We actually have a free evidence prep template on our website at Openroom.ca that walks you through exactly what to pull together — I’ll put the link in the description below. The landlords who use something like this from day one are always the ones who come out ahead.

The 72-Hour Rule

Next - Here’s what I call the 72-Hour Rule. This one’s specific to landlords in Ontario, but there is an equivalent in other provinces so look for something similar wherever you live.

So at this point in the process, the sheriff finally shows up and kicks someone out. And, awesome - you’d think the nightmare is over. But it’s not. Here’s what you need to know: The tenant actually has a 72-hour window where they’re allowed to come back and get their stuff. You’re legally required to give them access between 8 am and 8 pm.

It’s frustrating, and it feels totally unfair, but if you decide to throw their life on the sidewalk or mess with their belongings during those three days, you can end up owing them money. I’ve seen landlords do all the hard work to win an eviction, only to get screwed over at the finish line because they didn't know the rules for this 72-hour window.

Again, if you’re not in Ontario, just do a quick google search for how this works in your area. Other provinces may differ in their Sheriff eviction procedure. They might have “bailiffs”. But overall the idea is to be real careful about how you handle your tenants’ moving out after an eviction.

Screening Saves You

Next up: Screening saves you. It is perhaps the biggest thing you can do to avoid all this headache.

If I’m being totally real with you... most of that $35,000 I lost? It was my own fault. I was just bad at screening. I didn't want to be "that landlord" who was too judgmental, but that mindset cost me a fortune. We live in a world where tribunal decisions and court orders are public—the red flags are usually right there if you actually look for them.

But so many of us—me included—decided to just rely on a gut feeling or an employment letter. Some just get a credit score supplied by the tenant applicant - That’s just not enough. When you do the heavy lifting upfront, you find the tenants who actually value accountability. I learned the hard way that prevention is always going to be way cheaper than trying to chase someone through Small Claims Court later on.

But for most landlords we’ve talked to, they’ve found it’s really hard and annoying to do.

And thats why we built Openroom, a platform where you can search up your potential clients to see if they have any past court orders.

I’ve also made an entire 11 page guide on how you could be better screening your tenants, with free tools and more. I’ll put that in the description as well.

Hobby vs. Business

This one was the biggest mental shift for me.

I had to stop seeing myself as just a landlord with a rental property and start acting like a housing provider running a real, regulated business. I mean, you’re providing a safe place for someone to live, and that comes with a mountain of rules. You have to protect your assets and keep your records perfect.

You really have to ask yourself: am I running a hobby, or am I running a business? Because if you treat this like a little side-hobby, you’re leaving yourself wide open to massive liability. Once I made that switch in my head, everything else actually started to make sense.

The Reality of the Stress

And finally - I’ll be honest with you—the money wasn't even the worst part.

Losing $35,000 sucked, obviously. But the exhaustion really broke me. Just the endless waiting, the "not knowing," and the feeling of being totally helpless while my own money was draining away to cover someone else's rent. You’re here following the laws but the other party isn’t; and yet somehow you’re the one paying the price for it. It’s mentally, physically, and emotionally draining. And a really dark place to be.

But the reason I’m sharing all of this is because I want you to know it gets better once you understand the system. When you aren't just "reacting" to every little problem and you actually know the steps, you can finally start sleeping through the night again. That peace of mind is worth more than the rent checks.

Recap

So, if I could go back and talk to 23-year-old me...

I’d tell her three simple things: Build a structure so you don't lose your mind. Keep the paperwork so you don't get emotional. And for the love of everything, screen your tenants so you don't end up in court. Bad debt is extremely hard to get back.

If you need help doing that, we’ve built a tool at Openroom to help landlords do exactly that.

Openroom collects public tenancy records and connects them to the broader financial credit system to help you make informed decisions on who to rent from and rent to.

Because despite all the horror stories… you absolutely can build generational wealth and take care of your family doing this—I still believe that 100%. You just have to be smart enough to learn the system. And have the tools to do things right. I’ve worked with thousands of landlords now, and my goal here is to share everything I’ve learned so you don’t have to go through the same mess I did. Subscribe and click here now to watch this next video.

• Openroom — Court Order Search Engine: A Canadian platform that makes public tenancy court orders searchable so landlords can screen potential tenants for past rental disputes before signing a lease.
• Openroom — Court Order Search (Direct Search Page): The direct search tool on Openroom where landlords can look up specific court orders and filings by name or address.
• Free Evidence Package Preparation Template: A free downloadable template that walks landlords step-by-step through organizing and preparing their evidence package before a Landlord and Tenant Board hearing.
• Free Tenant Screening Guide (11-Page Checklist): A thorough 11-page checklist of the top tenant screening best practices from property managers and landlords across Canada, with free tools included.
• Free Eviction Day Prep Template: A free 23-page guide that walks landlords through everything they need to prepare for and manage eviction day, including the 72-hour rule for tenant belongings.
• Openroom Education Hub: Openroom's full library of practical articles, templates, and downloadable resources covering all aspects of Canadian landlord-tenant law and property management.