In this solo episode of The Country Club Podcast, host Diana Cassidy-Bush kicks off the new year with a refreshing, grounded conversation about real estate goal-setting—one that prioritizes clarity, lifestyle, and long-term planning over market predictions and media noise.

With headlines shouting forecasts and opinions at every turn, Diana offers a calm counterpoint: planning beats predictions every single time. She walks listeners through how to slow down, reflect on where life has actually landed them, and use real estate as a tool to support—not complicate—the life they want to build.

Whether you’re considering buying, selling, downsizing, upsizing, investing in a cottage, or simply getting organized for the future, this episode provides a simple, realistic framework for thinking about real estate in one-, three-, and five-year horizons. It’s thoughtful, reassuring, and deeply practical—perfect for anyone who wants to move forward with confidence instead of pressure.

Timestamps

00:00–00:45 – Welcome to The Country Club Podcast & show positioning

00:45–01:33 – Why this conversation matters right now

01:33–02:24 – January noise, reflection, and real life priorities

02:24–03:30 – Predictions vs. planning in real estate

03:30–04:15 – Why your home should support your lifestyle, not stress it

04:15–05:15 – Lifestyle questions driving real estate decisions

05:15–06:15 – Country living, cottages, and lifestyle shifts

06:15–08:15 – Starting where you actually are (without judgment)

08:15–09:45 – Common buyer mistakes in a noisy market

09:45–10:45 – Interest rates, timing myths, and financial comfort

10:45–12:30 – Seller mistakes: pricing, renovations, and strategy

12:30–13:15 – Strategy vs. seasonality

13:15–14:30 – The 1-, 3-, and 5-year planning framework

14:30–15:15 – Asking better questions about your future

15:15–16:30 – Planning as a way to create options, not pressure

16:30–17:30 – Closing thoughts, planning worksheet & next steps

Notable Quotes

“Planning beats predictions every single time.”

“A good real estate plan isn’t about guessing the market—it’s about understanding what you want your life to look like.”

“Your home should support your lifestyle, not keep you up at night.”

“Good strategy will almost always outperform good timing.”

“When you focus on direction instead of decisions, you give yourself time—and time creates clarity.”

Key Takeaways & Value for Listeners

1. Tune out the noise.

Predictions change weekly. Your life goals matter more.

2. Start where you are—honestly.

Real planning begins with acknowledging your current season without judgment.

3. Avoid rushed decisions.

Most real estate mistakes come from reacting, not from lack of information.

4. Think in layers, not deadlines.

The 1-, 3-, and 5-year framework creates flexibility and confidence.

5. Let real estate serve your life.

Homes, cottages, and investments should support how you want to live—not the other way around.

Resources Mentioned

1. Real Estate Planning Worksheet – Linked in the show notes
2. (Designed to slow the process down and help clarify...

In this highly informative episode of The Country Club Podcast, Diana Cassidy-Bush welcomes Chartered Professional Accountant Ben Bryden from Wilkinson & Company to break down one of the most misunderstood and most consequential topics in real estate: capital gains tax.

Ben walks listeners through the whirlwind of tax changes proposed since 2024, explaining what was supposed to happen, what actually happened, and what property owners should know as we approach 2026.

Whether you own a cottage, rental, farmland, or you’re thinking about selling in the next few years, this conversation gives you the clarity you need to plan confidently and avoid surprises.

Key Takeaways

1. The Capital Gains Inclusion Rate Remains at 50% as of this recording

Despite the upheaval from 2024–2025, the proposed increase to a ⅔ inclusion rate was cancelled in March 2025, leaving the long-standing 50% rate in place. This eliminates the urgency sellers once felt but future budgets may still bring change.

2. Timing Matters—Your Income Year Affects Your Tax Bill

Consider selling in a year where your income is lower to reduce the marginal tax rate applied to your gain. Selling early in a calendar year can defers tax payment to the following April.

3. The 12-Month Rule Automatically Applies

If you sell a property within 12 months of buying it, the profit is generally treated as business income (100% taxable) rather than a capital gain (50% taxable). Only specific life events may qualify for exemptions.

4. The Principal Residence Exemption (PRE)

For people with multiple properties (house + cottage), thoughtful planning is key. You must choose which property to designate for PRE based on accrued gain per year. If you use the PRE on a cottage sale, future gains on your primary home may become taxable.

5. Mixed-Use Properties Have Special Rules

If part of your home is used for rental or business purposes:

• You may need to apportion the sale value between personal and income-producing use.
• Using more than 50% of your home for business can jeopardize the PRE entirely.

6. Land Size Matters

The principal residence exemption typically covers the home + up to ½ hectare (1.24 acres) of land. Additional land may be taxed separately unless you can prove it’s necessary to the home’s use.

7. “Change of Use” Can Trigger a Taxable Event

If you convert a principal residence into a rental (or vice versa), the CRA treats it as a deemed disposition—a taxable capital gain—even if you don’t sell the property. You can avoid this by filing a special election with your tax return. Missing the election can result in penalties and unexpected taxes.

8. Keep Every Receipt for Capital Improvements

There is no 7-year rule for cost-base documentation.

• Improvements that increase value (steel roof, addition, upgraded countertops) raise your adjusted cost base and lower your eventual capital gain.
• Repairs that simply restore condition (new shingles, repainting) do not count as capital improvements.

9. Estate Transfers Can Trigger Capital Gains

When someone passes away:

• Property transferred to a spouse rolls over tax-free.
• Property transferred to children triggers capital gains at fair market value.
• Large real-estate-heavy estates may face liquidity issues without planning.

10. Special Rules Apply to Farm Properties

Farms actively used in a farming business may qualify for:

• The Lifetime Capital Gains Exemption (LCGE)—now up to $1.25M
• Or special rollover provisions for transferring farmland to...

In this episode, Diana Cassidy-Bush sits down with Brian and Joanna Milligan, owners of Milligan Meats — the beloved local butcher shop that’s become a cornerstone for both year-round residents and weekend cottagers.

What started as a dream to stay close to home and community has turned into a thriving business built on passion, trust, and old-fashioned service. The Milligans’ share how they took a leap of faith, transformed a massive building into a welcoming local hub, and created a workplace that feels like family.

Whether you’re a small-town entrepreneur, a weekend visitor, or someone dreaming of your own “someday” business, this episode is full of inspiration, laughter, and lessons in leading with heart.

TIMESTAMPS

00:00 – 02:00 | Welcome to The Country Club Podcast — Diana introduces the Milligans and their story of starting Milligan Meats in Cloyne, Ontario

02:00 – 05:00 | From Alberta to Ontario — How Brian and Joanna met and how his lifelong butchering experience led to the dream of owning their own shop.

05:00 – 07:30 | Taking the Leap — Buying the building, trusting instincts, and Joanna’s creative vision that shaped the shop’s welcoming aesthetic.

07:30 – 10:30 | Creating the Milligan Experience — Why “old-fashioned” customer service never goes out of style.

10:30 – 13:30 | Building a Happy Team — The Milligans’ share how they cultivate harmony, fun, and respect among staff.

14:00 – 17:30 | Supporting Local, Building Community — How the shop supports farmers, bakers, and artisans; plus a touching story about a local charcuterie board maker.

17:30 – 20:30 | Seasonality and Growth — From summer crowds to hunting season, the rhythm of small-town business life.

20:30 – 24:00 | Adaptation and Expansion — Growing the team, expanding products, and balancing busy seasons with purpose.

24:00 – 28:00 | Secret Ingredients & Customer Favorites — Rib eyes, hamburger patties, barbecue sauce, and those famous chicken bobs.

28:00 – 30:00 | Final Reflections — The power of loving your work, giving back to the community, and finding joy in small-town life.

NOTABLE QUOTES

“I design everything by feel. When it feels right, I know it’s right — and so far, that hasn’t led us wrong.” — Joanna Milligan

“How can you not love your job when it’s all built around community, laughter, and good food?” — Diana Cassidy-Bush

KEY TAKEAWAYS

• Big Dreams Don’t Need A Big City: You can create a thriving business in your small town.
• Follow your instincts: Big dreams often start small — and scary. Trusting your gut pays off.
• Create experiences, not transactions: The Milligans built their success on connection, conversation, and care.
• Community is everything: Supporting local makers and farmers strengthens everyone’s success.
• Growth can be joyful: Even long hours feel lighter when your work aligns with your values.

RESOURCES & LINKS

• Milligan Meats, Coyne, ON — Visit in person or follow on social media for product updates and local stories.

Connect with Diana Cassidy-Bush:

Facebook: https://www.facebook.com/DianaCassidyBushRealEstate/

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