The risk of buying first is financial, not emotional. A bridge loan or a rushed sale to make a firm offer deadline both cost money, and a seller who has not yet listed is negotiating a purchase without knowing exactly what cash they will have on possession day.
Selling first with a longer possession date, often negotiated at 60 to 90 days, gives you room to find the next home without a second mortgage payment stacked on top of the first. Your real estate lawyer builds that timeline into the purchase contract once you have an accepted offer.
For a downsizer working inside a six-month window, sequencing matters more than speed. Get your hand-reviewed valuation from Joel Dyck.