So this is what you are trying to do?
I am reasonable certain it is not to code to have a dimmer connected to an outlet.
I was thinking you were doing something like this:
With this setup, you dont need a bypass, and you could use either a red series dimmer or red series switch (it would need to be red series to work with your Iris outlet though because your hub would need to process the scenes and relay the message).
If you use the same setup as above, but also replace the outlet with a zwave outlet, you could use a red or black series switch and directly associate the devices (less lag and no true reliance on the hub)