I planned ahead and just dropped 2 outlets (each on it's own circuit) ahead of time. Was easy since I they are off the sub panel that feeds the solar system (or is that vice versa?). Since I work from home, I only charge like once a week, and now that PG&E shifted off-peak hours, I can plug in after my wife leaves for work.
However, in the event that we need to charge at the same time, I just leave my portable plugged into one outlet and back the car in so I can hook up to that. Easy to just remove the cord from the adapter so you're not wearing out that 14-50 a lot. Note from pictures, that it is easy to extend an outlet along the wall to move the charger to the front of the garage. This makes it capable of reaching both cars. I had planned to leave it at the front (installed there for the Leaf), but my wife was not having any of this "back your car in every day" stuff.
Also note, I highly recommend you let her park closer to the charger than you. ;-)
Ps. Apologies for the wrinkly decal application, I suck at wall paper! Planning to CNC a supercharger "half shell" that will look real when it's installed.