His situation is not far different from mine when I was his age, except his is maybe better than mine.

When we married, we applied for HDB flat but was told the waiting time would be 2.5 to 3 years. We waited for 1 year, went for balloting for left-over units but was still unsuccessful. We decided not to wait any more , and decided to plunge head on into private property. We bought a small 2 bedroom unit, paid for it with whatever savings we had and took loans for the remainder.

Then came the children, and we decided to upgrade to a bigger unit. But because we already owned private property we could not buy a new HDB flat any more, so we bought a bigger 3 bedroom private property. We took on a total of 2 loans!

Just before we could off load the smaller apartment, the gulf war started and property price plunged! We decided to hold onto to the unit and rent it out at very low rental. It was quite a terrible belt tightening time for us, and there were months where we had negative savings. We held on to both units for more than 10 years! and living very frugally (except for the car), all our holidays were self drive holidays to M'sia (Cameron, Genting, Taman Negara, Melaka etc). They were cheap and good holidays nonetheless.

Then came the MRT stations announcements, and prices started to recover (no, not recover, but sprang up!). Our small apartment was enbloc giving 3x what we paid for.

We immediately bought another 4 bedroom apartment with the enbloc windfall, moved our now bigger family into it, and rented out the 3 bedroom unit. Within 2 years, the 3 bedroom apartment also went enbloc but the returns not so fantastic.

Again, we used the money to buy yet another condo unit. This time not to stay but for rental income.

Looking back, if you ask me to do it again, I would say no way. It was scary time for us, But sometimes fortune favours the brave. Why? Because when I look at my classmates who went the HDB way, they are still staying in HDB. That's 30 years since we graduated.

Nothing wrong in staying in HDB flats, but they missed the exciting property cycles, and the fortune they could have made. Networth wise, I am guessing that ours are higher primarily because of the private property gains we had. They are letting on that they have around $2m to $3m but we have above $5m