House is not money. (Agree) When you are staying in it, e.g. HDB
When you are young and can get a 5 room HDB would you go and get a 3 room, if yes why. (Depends on price. But if OCR HDB generally the advice is to go for larger one - first bite should take a sizeable one. But some get 3 room with the hope of getting a second private property 5 years down the road when children comes.)
When you are old and want to upgrade to a bigger property, would you advise to go ahead, if yes why. (Depends on family situation. If large cash hordes and price is low, why not?
House is not money when you can just build more in another area and let the house rot, can you do it in Singapore (catch no ball, but some kinds of hdb upgrades allow adding area).
The three laws of Kelonguni:
Where there is kelong, there is guni.
No kelong no guni.
More kelong = more guni.