The tricky part about Singapore’s residential market is its dynamism: cooling measures can appear overnight, and the supply of housing is subject to five-year feast-and-famine cycles. These can make a lot of otherwise sensible housing decisions at that time look… well, dumb in hindsight. We’ve collected some stories of home buyers and investors, who can’t believe some of their previous decisions. Perhaps there are lessons to be found in the following:

1. Deciding to wait for “temporary” cooling measures to end 

GT had just missed the deadline to purchase a second condo unit, back in 2011. He says that: “Around 2011, we were considering if it was worth it to buy a ‘mickey mouse’ unit, because my daughter was renting a flat there with her partner. So we thought they can live there until they buy their own place, and later we can rent it out. But we ding-donged on the decision, and at the end of the ...