I wonder why we can't simply use shares trading as a way to distribute capital gains over few years. Example. Say you bought a property for 400K in 2010. After 10 years, selling for 700K. Taxable CG = 300/2 = 150K. To spread the above between two years, you buy shares in 2018 for say 500K. Say 250K worth of shares gone up by 40% and the other went down by 40%. In 2019, sell those shares gone up in value. Taxable CG = 100/2 = 50K. In 2020, sell those shares gone down in value. That is a 100K loss. Add this shares loss to the property gain = 200K gain Taxable CG = 200/2 = 100K. If the trading is done over more years then it becomes even more effective.