Business Succession – Tompkins Insurance

All Articles Business Succession Capital Gains Capital Loss Carry Back Planning Charitable Gifts EOTs Post-Mortem Planning Trusts

March 11, 2026

An update on legislation in progress and draft legislation not yet introduced

Here is a snapshot of the various legislative measures we’ve had on our radar.

Florence Marino

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All Articles Business Succession Non-Tax & Practical Issues

October 8, 2025

Restoring Trust When Relationships Break: From Brokenness to Belonging

In family enterprises, trust is critical - it shapes not only personal relationships but also how resources, legacies, and responsibilities are shared across generations. Learn how families repair broken trust.

Guest Author

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All Articles Business Succession Capital Gains EOTs Post-Mortem Planning

August 27, 2025

Summer reading of the legislative kind

The August 15, 2025 package of draft legislation addresses some of the tax legislative back log.

Florence Marino

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Business Succession Non-Tax & Practical Issues

June 11, 2025

How to Pass the Torch in a Family Business—Without Burning Bridges

We are fortunate to partner with Amy Castoro of The Williams Group to guest author our latest TOMPKINSights that provides tips for navigating the tricky handoff between generations.

Guest Author

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All Articles Business Succession

October 16, 2024

A business succession story – As told by the Tax Court

A tax case chronicles the story of a family business succession with a happy ending.

Florence Marino

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All Articles Anti-Avoidance Estate Freezes

October 2, 2024

CRA Guidance on Mandatory Disclosure – Contingent fees

CRA guidance on mandatory reporting says referral fees in respect of estate freeze transactions and the acquisition of life insurance do not require mandatory reporting. Positive for mainstream non-aggressive tax planning connected to life insurance…

Florence Marino

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All Articles Business Succession EOTs Life Insurance Tax Trusts

July 31, 2024

Legislative loose ends

For an update on enacted tax legislation and some of the loose ends we’ve been following.

Florence Marino

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All Articles Anti-Avoidance Business Succession Estate Freezes

March 27, 2024

The new GAAR is already getting warmer

More good news from the CRA on the new GAAR. Common tax and estate planning transactions that were not GAAR-able before are not going to be GAAR-able now.

Florence Marino 0

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All Articles Business Succession EOTs Trusts

February 14, 2024

Employee Ownership Trusts – An unchartered option for sale of business in Canada

Proposed tax measures provide a framework for a new business succession planning option. Will Employee Ownership Trusts take hold in Canada as a viable sale of business option?

Florence Marino 0

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All Articles Anti-Avoidance Business Succession Intergenerational Business Transfers Life Insurance Tax

December 14, 2023

Tax Legislation tabled – Some highlights

Bill C-59 implementing many measures from the 2023 Federal Budget is in progress. Here are our comments on some of the highlights.

Florence Marino 0

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Business Succession11

An update on legislation in progress and draft legislation not yet introduced

Restoring Trust When Relationships Break: From Brokenness to Belonging

Summer reading of the legislative kind

How to Pass the Torch in a Family Business—Without Burning Bridges

A business succession story – As told by the Tax Court

CRA Guidance on Mandatory Disclosure – Contingent fees

Legislative loose ends

The new GAAR is already getting warmer

Employee Ownership Trusts – An unchartered option for sale of business in Canada

Tax Legislation tabled – Some highlights

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