> Did this behavior start with the coda of Office Space or has it always been a thing?

No, it's such a cliche that's why Office Space chose to use it.

The movie Lost in America explores this theme much more generally.

The funniest thing about the end of Office Space is that by "dropping out" of software during the Y2k era and entering the construction field, the protagonist is just swapping one bubble for another, software for housing.