Rebuilding Wealth After Divorce: Sarah Coupland on Ontario Multifamily, Distressed Properties, and Creative Financing
By Erwin Szeto | Co-Founder, iWIN Wealth Planning
Recorded: May 2026
Host: Erwin Szeto, Truth About Financial Independence for Canadians
Guest: Sara Coupland, Real Estate Investor
Real estate investing is easy to talk about when markets are rising, financing is available, and the portfolio is growing. It gets much harder when life changes, assets must be sold, and the market no longer supports yesterday’s valuations.
In this episode, Erwin sits down with Sarah Coupland, a long-time Ontario real estate investor, coach, construction operator, and owner of TAG Property Management. Sarah has been investing since 2007, built a personal portfolio of more than 60 doors, and manages about 300 units for herself and other investors.
She also specializes in the kinds of properties most investors avoid: distressed multifamily buildings, mixed-use assets, older properties, and renovation-heavy projects that banks often will not finance. Now, as she works through the sale of her portfolio during divorce, she is also rebuilding from the other side using joint ventures, private money, and a more intentional strategy.
Selling a Portfolio in a Difficult Ontario Market
Sarah’s portfolio once included more than 60 doors. Today, because of her divorce, she is liquidating assets she had expected to keep long term. That process has forced her to reassess market values, buyer psychology, and the emotional side of letting go.
One of her biggest lessons is corporate structure. Most of her properties were owned in corporations where she and her spouse were 50/50 shareholders, but Sarah held the controlling shares. That made the disposition process smoother because she could deal with lawyers, realtors, and purchasers without every decision becoming a back-and-forth negotiation.
For investors building portfolios with spouses, partners, or joint venture investors, this is a major lesson: ownership and control are not always the same thing. The structure you set up when times are good can determine how manageable things become when life changes.
Distressed Multifamily Is Not for Beginners
Sarah specializes in highly distressed properties. One featured example is her 12-unit mixed-use building at 144 King Street West in Cobourg. The property had major deferred maintenance, a fire order against the third floor, wildlife inside the building, and units that were not suitable for habitation.
The project was massive. Sarah purchased the building for approximately $700,000, structured an 80% to 85% vendor take-back mortgage, capitalized the interest into the purchase price, used private money and deferred payments, and ultimately ended up with about $1.7 million invested after a renovation budget of roughly $1 million.
The property is now listed around $2.6 million, with roughly $21,000 per month in rent and a cap rate around seven, according to Sarah’s estimate during the conversation. Tenants pay utilities, the building has been extensively renovated, and much of the heavy lifting has already been done.
The story is a strong example of forced appreciation, but it also highlights why these deals are not simple. Heritage requirements delayed the project by roughly six months over window requirements. An engineering miscalculation created an additional $80,000 electrical issue. The renovation took about two and a half years instead of the expected year and a half.
That is the reality of distressed real estate investing: the upside can be significant, but the execution risk is real.
Why Old Buildings and Mixed-Use Properties Can Work
Many investors avoid old buildings, heritage districts, commercial units, and tertiary markets. Sarah often leans into them because lower competition can create better pricing.
Her strategy is not to buy anything old blindly. It is to understand what can be fixed, what needs to be budgeted, what the market will support, and whether the numbers still work after realistic contingencies. She has also found that commercial tenants can add stability, and that commercial landlord-tenant issues are often simpler than residential issues under Ontario’s Landlord and Tenant Board system.
That said, financing can be difficult. Mixed-use properties often do not fit neatly into standard CMHC or bank financing boxes. Sarah has used private lenders, vendor take-backs, seconds, and non-bank financing to make projects work when traditional lenders would not.
Investor Appetite Is Returning, but Discipline Still Matters
One of the most interesting parts of the conversation was Sarah’s take on today’s Ontario real estate market. On the sales side, she is seeing buyers still searching for discounts and often not believing the market has bottomed. On the acquisition side, however, she is also seeing aggressive activity.
One off-market property she analyzed received 11 offers in three days and sold about $60,000 over asking. Another rough Peterborough triplex from a wholesaler sold over asking despite needing extensive work.
Sarah’s conclusion is balanced: investors are starting to come back, but she refuses to chase deals. She works backward from conservative resale values, renovation budgets, investor return requirements, and contingency buffers. If the numbers do not work, she lets the deal go.
That discipline matters in a market where comparable values can move quickly. Sarah shared a recent flip where expected resale values dropped from about $550,000 to $530,000 during the renovation period, and the property ultimately sold for $505,000. The deal still made money, but only because the numbers had enough room.
LTB Challenges, Renovictions, and the Reality of Bad Buildings
Sarah also spoke directly about Ontario’s landlord environment, including renovation-related bylaws and the pressure placed on private landlords to carry low-rent or non-performing assets.
Her view is pragmatic. She respects housing needs, but believes governments should not expect private landlords to subsidize low-income housing indefinitely, especially when mortgage costs, repairs, insurance, and taxes continue rising.
In distressed projects, Sarah says she often approaches tenants honestly. If the building is unsafe, she explains the work required, offers compensation, helps with moving, and documents the process properly. She is not evicting for sport; she is trying to fix buildings that may have water pouring down walls, electrical problems, structural issues, or unsafe conditions.
For Landlord and Tenant Board matters, her advice is simple: communicate clearly, document everything, be honest, and bring evidence. If you made a mistake, admit it and move on. If you are at the board, make sure you are there for a valid reason and can support your position.
Becoming a Full-Time Investor Is Not Retirement
Sarah offered one of the most honest answers in the episode about becoming a full-time real estate investor. Too many people market it as “retire today” or “quit your job and become financially free.” Sarah’s reality was different.
She worked as a financial advisor at CIBC, renovated after work, ate on the go, and spent evenings and weekends doing the hard labour. When she eventually left her job, she did not simply jump into the unknown. She created supplemental income through property management, bought a fourplex, and worked with joint venture partners and private money.
Her warning is important: becoming a full-time investor is not retirement. Often, it is trading one job for another. The key is to build systems, income streams, a team, and a business that can eventually give you time back.
Sarah’s personal goal was to be off when her daughter was off during the summer. With coaching and intentional planning, she eventually built rules around her acquisitions. If she did not have an offer accepted by the end of March, she stopped buying until after summer. That discipline helped her protect the life she was investing for in the first place.
Education, Action, and Coaching
Sarah credits much of her growth to education and community. She mentioned Durham REI and Quinton de Souza as important influences, especially in learning about RRSP mortgages, joint ventures, flips, BRRRRs, and vendor take-back mortgages.
Her final advice for investors is straightforward: get educated, build your network, take action, and consider coaching when you are ready to move beyond basic investing. Her coaching is not aimed at complete beginners. It is better suited for investors who already own properties and want to move into multifamily, renovations, portfolio strategy, and more intentional investing.
Sarah’s story is a reminder that financial freedom is not always a straight line. Sometimes the portfolio changes. Sometimes the market changes. Sometimes life changes. But with the right structure, conservative numbers, strong relationships, and the willingness to rebuild, real estate can still be a powerful path to wealth for Canadian investors.
How to Connect with Sarah Coupland
Sarah can be reached through her website at SarahCoupland.ca or by email at Sarah@TAGProperties.ca. Investors interested in her listed properties can also connect with Anita Bongers-Lewis and Chris Lewis at Doors to Wealth Real Estate.
Quick Answers
- How many units does Sarah Coupland manage?
Sarah Coupland manages about 300 units through TAG Property Management, including properties for other real estate investors. - How many doors did Sarah Coupland own?
Sarah’s personal real estate portfolio was over 60 doors before she began liquidating assets during her divorce. - What type of real estate does Sarah Coupland specialize in?
She specializes in distressed multifamily, mixed-use, and older Ontario rental properties where value can be created through renovations and better management. - Why does Sarah Coupland use private money and joint ventures?
She uses private money and joint ventures because many distressed or mixed-use properties do not fit traditional bank financing, especially during construction or major renovations. - What is Sarah Coupland’s opinion on the Ontario real estate market?
Sarah believes Ontario still has real estate investing opportunities, especially in small multifamily properties, but investors must be conservative with numbers and contingencies. - What advice does Sarah give about becoming a full-time real estate investor?
She says becoming a full-time investor is not retirement; it is often trading one job for another unless you build income, systems, and a team.
Want the Whole $100,000 Strategy Walked Through Live?
This Saturday — May 30, 2026 — I’m hosting a free training called the Zero-Down Wealth Strategy. It’s hybrid: in-person at the iWIN office in Oakville, or join on Zoom from anywhere. Hard start at 9:00am Eastern, hard stop at 10:30am.
In those 90 minutes, I’m walking through:
- The complete $100,000 investment loan structure
- The math — what $433/month actually buys you over 5 and 10 years
- Every loss scenario — what happens when the market drops 20%, 30%, 40%
- How this fits alongside (not replacing) a real estate portfolio
- Live Q&A — bring questions, bring skepticism
In-person seats are capped at 40 people and they always go. If you want to be in the room, register today.
Saturday May 30 — Hybrid (Oakville + Zoom): infinitywealth.ca/20260530
Tuesday June 2 — Zoom only at 8pm Eastern: infinitywealth.ca/2026060
Both events cover the same content. Pick whichever fits your schedule.
The Bottom Line
Canadian real estate isn’t dead. But the conditions that made it a passive vehicle for the average investor are gone. If you want to be an active operator and treat real estate as a business, more power to you. If you want passive, you have to look elsewhere — landlord-friendly U.S. markets, leveraged stock-market positions, small-business acquisition, and a few other paths the show will keep covering.
Diversify. Pacify. Get your time and your peace of mind back.
That’s the next chapter.
To Listen:
You’ve Built Wealth. Now It’s Time to Understand It.
You’ve Built Wealth. Now It’s Time to Understand It.
After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.”
Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live.
Download your free Wealth Freedom Blueprint
Final Thoughts
Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life.
That’s what iWIN Wealth Planning is here for.
This is how we’re creating predictable, stress-free wealth for Canadian families…
so you can enjoy the life you’re building.
Book your Wealth Planning Call
Sponsored by… Me!
This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.
Till next time—just do it. I believe in you.
Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto
Disclaimer
As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.
My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.
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