My dad bought his first property in another medium-sized city outside of Boston in the mid-80s and sold it in the early-90s for a near 50% loss. Luckily, he, like so many others in Melrose, has built up a ton of equity after owning our home for a few decades. So he’s made out ok.
I vowed to myself that I would never buy a house during a ‘boom’ period - I’m just sitting here waiting for a bust, even if it’ll take a few years to materialize.
I’m selling now and maybe buying later. Getting old enough it’s just for fun now. I did buy a piece of recreational land last year and put a trailer on it for hanging out. The heirs can sell it.