What I did during my more severe periods of procrastination:
Warning: very large image.
67km of new track,
122 stations,
7 lines,
2 regional tram-train lines,
2 new bridges
Maximum distance of less than 2km from a station for the entire city.
If only...
At Portland's 10M/km for tracks, stations and cars and including the price of the new bridges, it could be done for about $1B, but we'd need to bring Jean Drapeau back from the dead and I don't know how much that'd cost.