Count the cash you need at each step, not only the total. Buying first means paying the option money, the downpayment and the stamp duties before any sale proceeds arrive.
The two 6-month clocks start at different points. HDB's runs from the resale completion date of the flat you are buying. The ABSD refund period for a completed private home runs from its date of purchase.
A sale is not done when you find a buyer. The option period, HDB's resale application and completion all take time, so start the sale early enough to finish inside the deadline.
Some banks offer a bridging loan against the sale proceeds once the sale is firm. Ask about the conditions before you rely on one.
