I’d go with buying an investment property first, live in it or a year or so, then buy a main residence, for two reasons. Firstly, if prices continue to fall you lose less because your initial capital outlay was smaller, and secondly I would imagine, most investment properties such as condos have come down more in price than SFH’s at least in the $600k bracket.
I’d be very interested to know from anyone if now is a good time to start considering looking at investment condos/studios, and what sort of net return one can expect, for a cash purchase in the $250-300k ballpark?