this is really dependent of the type of housing. midlife is when you start needing to replace things and the downsides of the housing become way more apparent.

To give the example, brownstones became unpopular as it became apparent their designs resulted in high heating and AC bills since they were pretty drafty and poorly insulated. Only when they blossomed into being "historic" did people start valuing them enough to start fixing the problems and restoring them.