Cottage, Corporation, Concentrated Stock: Why the Will Alone Cannot Solve the Problem
April 23, 2026
BY: IAN ANDREW LAW
Clients often know exactly what they want to happen. One child should receive the cottage. The shares should be divided fairly. The business should stay intact. The will records that intention.
The harder question is whether the underlying assets are structured in a way that lets the family carry out that intention without triggering a fight, a liquidity crisis, or a forced sale. In estate planning, difficult assets usually need more than a direction clause.
Key Takeaways
• Some assets are hard to divide, hard to value, or hard to keep.
• Cottages, businesses, and concentrated investments often create outsized risk.
• The problem is usually structure, liquidity, or fairness of outcome.
• A will can express intention, but it does not remove the underlying pressure.
• The plan needs to anticipate how the asset will be carried, taxed, or equalized.
Why These Assets Create Special Risk
A cottage is emotional, illiquid, and often tax-loaded. A private corporation may have real value but no ready market. A concentrated stock position may expose the estate to timing risk if it cannot be diversified on a sensible schedule. Each asset creates a different kind of vulnerability, but the common feature is the same: the estate may not be able to implement the will cleanly without additional planning.
The Fairness Question Usually Arrives Fast
Even where there is no hostility at the outset, fairness issues develop quickly. If one beneficiary receives an illiquid or high-carry asset and another receives cash, is that actually equal? If the estate must sell something to equalize distributions, who bears the tax? If siblings are expected to co-own a cottage or business interest, what happens when their goals diverge?
Those questions are not solved by saying “my trustees may decide.”
What Good Planning Does
Good planning tests whether the intended gift is workable. That may mean modelling the tax, creating liquidity, setting governance rules, changing ownership, or deciding that a lifetime restructuring is better than leaving the full pressure to the estate. The legal document still matters. It just works best when it sits on top of a realistic plan for the asset beneath it.
A will is a direction document. Difficult assets also need an execution plan. Where the underlying asset is the real problem, better drafting alone is rarely enough.
Sources
• Income Tax Act, R.S.C. 1985, c. 1 (5th Supp.), including ss. 54, 70, 83, 88, 89, 146, 146.3 and 164.
• Estates Administration Tax Act, 1998, S.O. 1998, c. 34, Sched.
This article is for general information purposes only and does not constitute legal advice. Reading this article does not create a solicitor-client relationship. If you require advice specific to your situation, contact my office.