Updated June 2026. Originally published March 2023. In Singapore, owning a property is often seen as a marker of wealth and success. But between high prices, tighter loan-to-value limits and ever-rising stamp duties, the maths on a second local property has quietly stopped working for a lot of people. That’s why, back in 2023, I sat down with a Singaporean engineer named Weihan, co-founder of Byte Sized Investments, who had taken an unusual route: instead of buying his next property here, he’d been buying rental homes in the United States. At the time, he owned nearly a dozen. I recently caught up with him again. Three years on, Weihan and his wife Tracy now hold 27 US rental properties, collect roughly US$37,000 a month in gross rent, and have both left their corporate jobs in their 30s to do this full-time. Celebrating the closing of their 25th and 26th properties So I wanted to revisit the original conversation, update it for where things...