I have had OSS on many, many of my boarding passes as I live in YOW and almost always have to connect to get there.
I have NEVER (ie not even once!) seen any benefit from OSS. I ALWAYS have to go though security again.
A while ago i asked several employees in YYZ (Air Canada, YYZ Airport and CBA) and nobody even knew what OSS was.
So, I think its premature to say you wont have to go through transit security.
Maybe you wont have to collect your bags (I usually carry my bag so I dont know).
Please report back how it goes.
Oh- this has been discussed in detail:
http://www.flyertalk.com/forum/air-c...-security.html