All About Estates

Category: Insurance

Total 30 Posts

Cross-Border Insurance Planning – Some Basics

Cross-border insurance planning is tricky but understanding the basics can go a long way in assisting clients. This short article will review some of the key questions to consider in order to avoid potential pitfalls in life insurance planning. Who is the Owner, the Insured and the Beneficiary In the…

Continue Reading

ILIT – An Estate Planning Vehicle for the U.S. Person

An irrevocable life insurance trust (ILIT) is an estate planning vehicle worth some consideration for U.S. citizens living in Canada.  Many estate advisors are unaware that U.S. citizens subscribing to life insurance on their life will have the death benefits included in the value of their taxable estate for U.S….

Continue Reading

Corporately-Owned Insurance, Redemption Obligations and the U.S. Supreme Court

Canadian estate and tax advisors may want to consider the case Connelly v. Internal Revenue Service, No. 23-146[1] (U.S. 3/27/24).  The U.S. Supreme Court (“SCOTUS“) issued its decision on June 6th and it serves as a good reminder of the implications of corporately-owned life insurance in the context of cross-border…

Continue Reading

Further Assessing Drake’s Estate Planning Needs

Nearly two years ago, I wrote a blog post titled “Assessing Drake’s Estate Planning Needs”. The post looked at rap sensation Drake’s assets vis-à-vis his intent for his son Adonis to be the sole beneficiary of his estate, and the various considerations that he ought to have in planning for…

Continue Reading

INSURANCE TRACKING SHARES

If a taxpayer owns shares of a corporation and passes away, he or she is deemed to have disposed of their shareholding at fair market value (“FMV”) unless a tax-free rollover is applied (e.g., rollover to a surviving spouse). The disposition of shares may cause a tax liability. In the…

Continue Reading

When Leaving Your Premises for Medical Reasons and Never Go Back: Need a Plan

I do a lot of work in the insurance industry. Recently, I came across a court case which I thik is a cautionary tale for estate planners and executors. In Gregson v. CAA Insurance., 2021 ONSC 3041, Ms. Gregson was a property owner and name insured on March 17,2017 when…

Continue Reading

CPP: TO DEFER OR NOT DEFER

For several years now, clients and contacts (with more frequency of late, and that’s no accident) have been asking me: “Hey Steve, I am turning 65 shortly, do I apply for CPP now or do I wait – what makes more sense financially” Based on analysis provided by experts in…

Continue Reading