[winbig]

When did they solve the problem before?

High cost of living.
Low birth rate.
High COE.
High medical cost.
GST from 0 to 9%.
CPF cannot retire happily.
Work until die.
….

My opinion 

High cost of living. - govt cannot do anything about external factors but they can help by not increasing those water tax, transport fares, carbon tax, etc

Low birth rate. - this is another one govt cannot help directly. They can only provide incentives to have baby but if selfish/self entitled people such as sgbuffet exists, whatever incentives provided will not get them to start a family.

High COE. - we are a small island with efficient public transport. We are not like those big countries where public transport is not able to reach many places. 

High medical cost. - if not wrong, govt did subsidise a substantial amount. If u bothered to look at the bill, u will realise that

GST from 0 to 9%. - if everybody have sense of entitlement, want this, want that, everything also expect govt to pick a to subsidize, govt must increase their source of income 

CPF cannot retire happily. - there must be other reasons why one is not happy after retirement. Definitely not due to CPF. CPF only provide a source of income. How much u get depends on how much u save during working years.

Work until die. - So far, those old people in the company I've worked before, they work to pass time. Their children have grown up, if they don't work they feel bored at home. If we grow old and children have grown up or maybe don't have children, we need to think of what we are going to do everyday if we don't work. Are u able to plan daily activities to do when retired? Or just laze at home and wait to die?