Good points.
I am well aware of the Toronto store, SA's may be distant at first because they have people asking for quote bags all day long. Don't be intimidated by the store. Also, for your first time you may feel more comfortable going in and not being bothered anyways, which will allow yourself to acclimate to the store and culture. You don't need to be of any economic status to go into the store, go inside and walk around to see what they have. You may be surprised and like what they have and want to purchase something you may have never considered.
If you only want a quota bag, go the resale route.
Regarding your comment on exclusivity and not wanting to be part of a group that everyone can't be part of : You say you have purchased other luxury goods and handbags for many years already - do you realize you already are part of the exclusive upper class society that can afford to do so, as most people can't even afford LV, Gucci, etc.... So in all honesty you already are part of an exclusive group that everyone can't belong to.