If have the money to downpay the house, but cashflow is tight due to the mortgage loan. Should we still upgrade from HDB to condo? Currently in late 30s with 2 kids.

Realtor here. Hard to advise without knowing more. Also need to look at how much you have left after downpayment. Ideally you need to cater enough buffer just in case anything happens. Furthermore you have kids, the buffer is even more important in this situation.

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The fundamental is to never over stretch yourself. Make sure you have good exit plans in case of emergencies.

I heard some condo maintenance fees can be expensive.