I'm just trying to consider when is a good time to do such "upgrading".
Sell HDB now will not lose but won't earn much.
But selling HDB during recession would save more if condo prices fall more so perhaps make sense to wait for recession.
The health of the rental market will determine the market prices of real estate to a large extent. So, if the condo rental market continues to soften, condo prices will continue to come under pressure. For own stay or rental, this is something to bear in mind.
Our home is a consumption item. It would not be wise to overstretch our finances to stay in a more expensive home and I know a few people who overstretched.
If we are able to afford a condo quite safely (i.e. it does not impact our balance sheet badly and it is not reducing cash flow to a trickle), then, good.
If I had to sink further into debt and if my monthly cash flow is reduced drastically because of this purchase, I would worry.
Of course, always think about the opportunity cost. For example, if I had to dispose of income producing assets in order purchase this condominium, I would think twice.
Staying in a condominium does not give any financial security.
Personally, I do not think that the ABSD will be lifted soon. When interest rates start rising in a sustained manner, maybe. Just a guess.
However, you might want to ignore all that I have said as keeping your wife happy might be worth the price to you.
This is where I should stop talking to myself.
Wife wants to sell HDB flat to buy condo.