This is a reply to Ruby, a long time reader of ASSI, but it turned out to be quite lengthy. So, I decided to publish it as a proper blog instead. Ruby's comment and questions: My reply: Hi Ruby, Of course, the property agent would want you to sell your home and buy a new one (probably from him too). ;p Ask do you need to sell or do youwant to sell your home? Your home is a freehold property and does not suffer from lease decay. This is a fact. Aging freehold property? I don't understand why is that an issue. From the perspective of your home holding its value over time, what's wrong with that? Now, if you need more money for retirement and if selling your home is the only way to achieve this, then, you have to do it. Then, you can choose to eitherdownsize (rightsize) or downgrade ......