I still have to confirm if I am going to be able to go with (really hoping I can), but for the route, what about simply meeting ar N1 City (as normal), then along the N1, R300, N2, then Sir Lowry's Pass, Grabouw, Hermanus turn-off etc? Of course through Gordon's Bay, Betty's Bay etc is also awesome.
Imran, where was this road works? Trying to figure out where you are talking about just opposite Fisherhaven before Hawston?
For Chapman's Peak, maybe another breakfast run since that is an awesome run all on its own!