Your post had me thinking back to when I was in my late 30s, some 16 years ago. Our combined income then was similar to yours now. Times was hard for us. Here was what happened.

Years earlier when we got married, we applied for an exec HDB flat. When we were told we had to wait 3 years for it, we decided to buy a small private apartment instead. As our children grew they wanted their own rooms and with my parents staying with me, we upgraded to a 4 bedroom private property. We bought the bigger property first while waiting to sell our smaller property. Then the Asian Financial Crisis hit, and we were stuck with 2 properties and 2 loans!

Luckily we were "relatively young" then, we held on to both properties and rented out our smaller apartment for a song. Would you believe for only $900 a month!? For a further agonizing 10 years we held on to the smaller apartment, where at long stretches it remained vacant, because for that rental we were getting unsavory tenants. So we decided that we rather leave the apartment empty.

Then enblocs got into fashion, and we got 3 x what we paid for the small apartment. There was no looking back for us. With the money, we invested in another 4 bedroom condo for rental. And at the same time, our own 4 bedroom apartment also got enbloc-ed! Buoyed by the property magic, we bought yet another.

We are now staying in the newer 4 bedroom condo apartment with another brand new condo apartment for rental income. Both fully paid.

Looking back, my wife and I felt that had we waited for the HDB flat, we would still staying in the HDB.