You can see here Bison swings north around the existing houses and lots along Cadboro. Then swings back south near Kenaston. The right of way is the part that isn't green. Seems this is being maintained long term. I'll see if I can find the plans for the southeast area of Bridgwater. On this cadastral its still showing all the old lots as the one haven't been formally processed yet.
As for Brady, I'm going to assume it will remain as is. That's the City boundary, so Winnipeg will have no part in development to the west. Until something goes ahead there, I'll assume nothng will happen. Brady at the south end will be cut off as part of the PR 330 works, if it hasn't been done already. Access to 100 would be at either of the new Kenaston or PR 330 intersections.