In August 2021, the co-owner of the property management and rental business Nassau Property Partnership, located in London, Ontario, asked his brother, a senior partner in a tax firm, for help with the tax structure of various operational and strategic decisions, both for his business and personal affairs. The business managed well over the COVID-19 pandemic, but several recent major events required advice from an experienced tax professional. Regarding his personal life, the co-owner was considering retiring from his company, which was a partnership, and had already put down a deposit on a second home in Florida. He wanted to fund the remaining part of the purchase through either a sale of his business interests to his daughter or through the sale of his family cottage. However, both of these decisions may have repercussions.