Basing on $160k cash to pay for downpayment of condo to invest in while retaining your current HDB, the quantum value of the condo which you can purchase is in the range of $800k or below. Since you mentioned that you will be taking this purchase as an investment with your family member, the investment quantum could likely be higher.
There is unlikely to be much difference if you purchase a brand new EC or not since you will be occupying the brand new EC once TOP and purchasing the private condo under your family member, therefore your rental yield is likely to be the same.
With the uncertainty glooming over the real estate market, are you comfortable in putting in more money for a self occupied property.
To sum it up, I'd say it makes little difference monetarily in my opinion for the options you have listed. In terms of comfort for self occupation in HDB or EC, it will depends on your family and lifestyle.
Let me know how I may assist you further.
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