You're using products based on some of the most proprietary software/hardware around, and you're asking if an open-source operating system can do it? Maybe if you weren't suckered into using such closed crap it would work. There are plenty of alternatives that would work. All that being said, depending on what ipod you have, it can. And depending on how everything is setup for the last part, it also can. Next?

I dunno what you're talking about, Bioshock works fine on Vista 64 for me