I actually imported mine back in April (long easter weekend) and the process was painless.
I had indeed to bring the car to the authorized dealer in Ottawa but the process is simple and not that expensive at all.
All I did was ask the Porsche dealer in California to hook up the computer and set a flag to 'Canadian'. That cost me nothing as I was there for regular service.
Once in Canada, before taking the car to the authorized dealer, I brought it to a mechanic that worked for Porsche for several years (and now the guy that takes care of my car) and he did the DRL modification for me. I do not remember the total cost but was cheap.
Then I brought the car to the dealer. With the flag already set to Canada and the DRL done they had nothing to do at all with it. So I paid the $500 for their blessing and it was all good.
Again, it is a very simple process and considering the deals in the US, it is simply a no-brainer.
As soon as I pull the plug on an Aston Martin, off to the US again.
CR