If BTO is not an option, and SBF/ROF is out of reach (failed multiple times), the only option left is resale flat. Is buying an old flat (above 40y) more viable or a relative new flat (Less than 10y)?

I think it depends on your choice of living standards.. some don't mind old estates bc of its established amenities for a more convenient and comfortable stay.. if u read around, actually there are alot people who buy resale from old estates for the reason as the intention is purely for staying.. u can also choose to sell back your old estate to hdb I think to downgrade to studio apartment for retirement..

Hey! When buying an older flat, I second Zuhdy that you have to be sure that you won't need to sell either to cash out for retirement, or to upgrade to a new one.

Make sure that you don't outlive the remaining lease of your flat too!

Reason is because a HDB flat with a short lease depreciates very fast and is going to be very difficult to resell again.

A newer flat however, can still retain it's value well.

I would recommend not overstretching yourself though, if it's your first property. Go smaller, and upgrade later when the need comes.