[Docere]

In 1900, the Annex was probably Toronto's most elite neighborhood. It was certainly marketed as an upmarket community.

But in the 1920s it saw "rich flight" as many moved "up the hill." In the depression and postwar years, it was kind of of an old bourgeois neighborhood down on its luck. Of course in recent decades it has re-emerged as a desirable central city neighborhood but still retains a socioeconomic mix.

Rosedale is thought of as the same era as the Annex, but it didn't decline. It was high income even in 1960.

My guess: Rosedale was developed as a more homogeneous community (and there was more geographic sorting by class by the turn of the 20th century) and it was more contained from the city center due to the geography of the Rosedale Valley. Rosedale may be close to Yonge and Bloor, but its orientation and feel seems more "North Toronto" than "downtown." While the Annex orientation is more to downtown.