Now that I can actually post links...
We can deal with snow. This was on the Alaska Highway trip, on the way back. We took a detour to the Icefields Parkway, and it was snowing. Hard.

There were two separate points on this stretch where none of the wheels of the car were touching the ground, and we were going only with our momentum pushing us on the undercarraige. This was in a Carolla, and we're looking for a 4x4 for this trip, so in theory we're better off. Keep in mind that my friend and I have both lived in Boston for significant portions of our lives, and we defenitely have to drive in the snow.
Penguins - My guide book (and I know your opinion on Lonely Planet) says that there are two in/around Punta Arenas, one needing a boat tour and one that is better seen in the morning for lightning purposes. We're arriving at 2:00PM, so we'll see what happens. Punta Tombo is even in lattitude with Ventisquero Colgante, or at least close to it, so if we're going that far north it makes at least some sense.
Torres weather - Understood. Is there really any forecast that we can go with, or do we just go and pray? I understand that seeing something only once has the risk of weather not permitting you to see it at all. That's part of the risk of travel photography. Sometimes you get lucky...

And sometimes you do not. We'll do what we can to maximize our odds, of course. If we take multiple stabs at the Torres, that would be better, but we'll have to weigh that in our trip plans.
Schedule - Understood about border crossing times. It probably won't help that my travelling companion and I have different country passports. However, again, it's worth pointing out that an 18 hour day is *short* for us. Driving to 2-3am is normal, and all-nighters will happen on occasion. We're probably only coming here once in our life (maybe a time or two more if we're lucky, but you never know), so why would we waste more time than is absolutely necessary with sleep? Besides, some of the best photos are taken at night. We will probably only stay in a hotel for two nights on the trip - the first midway through to shower, shave, etc, and the second to make sure we're not committing crimes against humanity on our flights back to the US.
I will prepare a potential detailed schedule tonight.