I always enjoy reading your detailed analysis and professional advice in response to readers’ questions to support their decision making. This time, I hope you could also help answer my questions.

We are approaching our 50s with combined yearly income of ~$300K with 2 teenage (15-19) kids. We own a 4-room HDB in one of the cheapest estate and a freehold one-bedder in D11 (in equal shares) with no outstanding loan. As our HDB is now over 22 years old, I have been wondering if we should still keep it. I am also considering moving into a 3-bedroom condo in a more central/convenient location but have been put off by the ever rising ABSD (One of us is SPR.)

With our combined cash saving of ~$300K and CPF OA of $400-500K, should we sell one of our current properties and/or decouple, and get a 3-bedder condo for own stay? Would it still be possible to also buy