Yesterday, I was at a real estate tax consequences event in Oakville hosted by Paul D’Abruzzo. Fabio Campanella, a fellow CPA, shared some great insights on tax consequences most real estate investors often ignore. As a CPA in practice, I’m often amazed how much I learn from my fellow colleagues even in subject areas I’m very familiar with. I was impressed and walked away with clearer insights as Fabio masterfully and clearly simplified the four events that trigger capital gains. I share a highlight in this issue and I also highlight the struggles real estate investors have with existing non-performing investments. Remember, I’m here to help with your complex and simple tax issues. Enjoy and please remember to share this with everyone in your network:
1. No Profit? Fix It or Exit
This was one of the highlights of the presentation yesterday as I recall how I held on to my first real estate investment for over 10 years before exiting. It underperformed for many years and I held on because I know that time, oftentimes, will turn a poor investment into a good or great investment. While we ultimately exceeded breakeven with the investment when we exited, it was a poor decision to hold on for that long as we essentially underutilized our capital.
Here are a few takeaways if you have any leveraged investments in your portfolio:
- It’s important to regularly review the performance of your assets, at least annually to ensure you’re achieving your target returns
- Never ignore opportunities to enhance the performance of your existing assets. If you own an existing rental property, is there an opportunity to rent out the garage for additional income; add another unit or change use to maximize returns?
- Taking a capital loss on an investment is not a failure. It releases capital that can be deployed to other productive assets. In addition, capital losses are an asset from a tax perspective as they carry forward and can be used in the future to offset capital gains.
I know I’m likely sitting on some assets that could be performing better and I look forward to my consultation with Paul and his team to do a review of my portfolio. I encourage you to do the same, so feel free to consult with Paul here.
2. The Four Capital Gains Triggers
As Fabio highlighted in his presentation yesterday, most Canadians only think about capital gains when they “sell” something—but the Income Tax Act is much broader. Here are four key moments when a gain can be triggered, even if no money changes hands.
- Sale: The obvious one—when you dispose of capital property (like real estate or investments) for more than your adjusted cost base plus selling costs.
- Change in use: Converting a principal residence to a rental (or vice versa) usually creates a deemed disposition at fair market value, with elections available in some cases to defer the gain.
- Transfers: Certain transfers of title or beneficial ownership can be treated as dispositions for tax purposes, even within a family or to a corporation or trust.
- Death: On death, you’re generally deemed to have disposed of all your capital property at fair market value immediately before death, which can trigger significant capital gains in the final return.
If any of these might apply to you, it’s worth getting advice before you act—good planning can reduce or defer tax, protect the principal residence exemption, and avoid unpleasant surprises at sale or death.
3. Capital gains in plain language
I’m currently enrolled in CPA Canada’s Indepth Tax Course, Canada’s most reputed 3-year tax training program for accountants and lawyers practicing in tax. We recently completed a module on capital gains and I was amazed how complex this topic is. It is the most litigated tax topic in Canada and I can understand why as I read some of the relevant sections of the Income Tax Act.
Most Canadians know capital gains are “taxed differently” but don’t really understand how the rules work—or how much money is at stake if they get it wrong.
In my latest article inspired by the event I attended this weekend, I break down capital gains in plain language: what actually counts as a capital asset, how the 50% inclusion rate works in real life, what you can (and can’t) do with capital losses, and why planning matters so much if you own rentals, non‑registered investments, or a business. I also highlight key opportunities like timing your sales, using old losses properly, and planning ahead for a future business or property sale.
If you own assets with unrealized gains and want to keep more of your after‑tax wealth, this will be a very practical read.
👉 Read the full article here: https://kengreen.ca/capitalgains/
4. Ten Mistakes to Avoid as You File Your Personal Tax Returns
Most Canadians rely on DIY tax software and assume that’s enough—but the real cost is in the mistakes you don’t see.
In my latest article, I walk through 10 common (and expensive) errors I see every year: from over‑claiming self‑employment expenses and ignoring carryforwards, to missing powerful credits and mishandling CRA reviews. I also show you the key numbers you should pull from your return—your actual tax paid, average and marginal rates—and how to use them to pay less tax next year, not just “get a refund” this year.
If you’re serious about keeping more of what you earn in 2026 and beyond, this is a must‑read.
👉 Read the full article here: https://kengreen.ca/10mistakes/
5. Tax Webinars on Demand
Recently, we hosted webinars on personal and corporate tax tips and planning considerations.
On personal taxes, we shared some important updates on personal taxes ranging from the extended deadlines for charitable donations, reduction of personal tax rates, disability support deductions, alternate minimum taxes, trust filing, carbon rebates, first-time home buyers GST rebate, personal support workers tax credit, other tax credits/deductions, and many more…
If you run a business, you’ll learn how to:
- Decide if a corporation is right for your business (pros and cons)
- Stay onside with legal, HST, payroll, and compliance requirements
- Use smart compensation strategies as a corporate owner
- Navigate what’s new for the 2025 & 2026 corporate tax filing seasons
- Build tax-efficient wealth and minimize taxes using your corporation
If you missed the LIVE webinars or want to revisit, you can watch them on demand here: https://gmscpa.ca/webinars/