The only problem I see with the Turbo in winter time is ride height. As soon as snow builds up under the car, you're stalled.
But traction is fantastic and with the right winter tires, you don't have too worry too much.
The Cayenne Turbo is a different story: I drove one and I loved it. I'd say it is the most refined SUV on the market right now, even if I'm not a friend of it's design.
Driving in snow should be a pleasure with this beast, should be the most powerful "almost perfect" winter car.
The question is what your priorities are:
1. the E55 is the "Family 996 Turbo" but lacks traction and can be a pain in the a.. when it comes to slippery (even wet) streets. One reason why I'll soon get the 30% limited slip differential installed by AMG in Affalterbach (this option is
not available anywhere outside Germany, so don't bother to ask about it), hoping that the traction problems will be gone as I've been assured by an AMG guy.
No, the E55 is not the right car for canadian winters, even if you can raise the ride height which is pretty impressive.
2. the 996 Turbo is
the sports car, a beast, a highly refined product and without doubt one of the best 5 sports cars in the entire world. I'm not sure this is a car I want to drive in winter time but it is your money.
3. the Cayenne Turbo is the perfect SUV for sports car owners. Despite it's weight, it delivers practically the straight line performance of a Porsche 993 C2 up to over 140 mph (~224 kph). The electronic suspension is very good, allowing the Cayenne Turbo to be driven almost like a high power limousine. The E55 is different but I'd say that the Cayenne Turbo is somewhere between the ML55 AMG and the E55, probably a little bit more close to the E55.
It is the perfect winter car with winter tires, traction ends where the car has nothing to put grip on anymore.
The decision is yours, Vladimir.