Our current HDB resale flat is 35 years old and we only moved in 2 years ago. How do we gauge when is a good time to start looking for the next property?

The best time to start looking is of cos when 1. u got money and u are upgrading. 2. when u got no money and u are downgrading. All other reaaons mentioned to beat the market are rubbish. No way u can trade same unit for a new unit without incuring usually huge loss. There is no way u can dump your short lease unit on others for high price and same time get a similar unit with longer lease for the same price. Its like asking where to find big fat tortoise walking down restaurant kitchens

You would have lost a certain pool of buyers after your flat turns 40 years old. That's because buyers can't use their cpf for the flat after it is 70 years old. For flats that are in between 40-70 years old (meaning remaining lease of 60-30 years), buyer's age plus remaining lease must be at least 80 years for them to still be able to use cpf and/or take max loan. Or else they have to buy your flat using more cash. Unless your house is in a prime district and many people are willing to spend cash, I would say your flat loses value after 40 years.

Now would be a good time. I generally advise against 30yo flats as there is usually no upside (unless mrt built just beside the hdb) and the only way is down. Usually stagnant value from 30 to 40, then start depreciating. Maybe take a look at URA website to see if there will be any favourable developments at your area.

You got a few option for asset progression depends on your risk appetite.

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