A couple I met last year were both in their early 50s. Their condominium was almost fully paid, but as they began preparing for retirement, they realised that a large part of their wealth was tied up in the property. They were asset-rich, but the home did not generate the income they would eventually need after they stopped working. Their plan was straightforward: sell the condominium, move into a five-room HDB flat and invest the capital released to generate retirement income. This would reduce their housing costs and allow them to enter retirement with more liquidity and less financial pressure. The numbers worked. The rules did not. At the time, they would have had to sell the private property first, rent somewhere for 15 months and only then buy an HDB resale flat. That meant two house moves, more than a year of rent and prolonged uncertainty over the price of their replacement home....