Simon bought his first house in April 2015 and paid $600,000 for it, as well as paying stamp duty in the amount of $30,000. After living in it for 2 years, he commenced renting it out in April 2017. At the time, its market value was $650,000. After it had been rented out for a year, Simon had the entire house repainted, during April 2018, at a cost of $5,000. At the same time, Simon also put in new decking in the backyard of the house (there was no decking there beforehand). This cost $3,000 in wood and other parts. Simon did the work on the decking himself. He estimates that the labor would have cost $7,000 had he paid someone else to do it.
In 2019, Simon paid $5,000 in legal fees. The next-door neighbor to the house disputed ownership of the some of the land that Simon’s house occupied. The neighbor was unsuccessful in their claim.
During February 2020, Simon sold the house to his sister for $800,000. He estimates that the market value at the time was $900,000

Simon also inherited an apartment from his uncle in May 2017, which he immediately rented out. At the time, its market value was $500,000. His uncle had purchased the house in 1980 for $50,000 and had used it as a rental property. During May 2018, Simon took a $40,000 mortgage on this apartment, which he used to renovate the kitchen and bathroom. During May 2020, Simon sold this apartment for $700,000, with the purchaser agreeing to take over the remaining mortgage of $30,000 on the apartment.

During June 2020, Simon sold some shares for $250,000. These had been purchased in 2017 for $320,000.