A:AnswerSiri needs some kind of internet connection to work. So, if you were in the car on an iPod, and not near a wifi signal then Siri would not work.
A:AnswerNot without great difficulty. Apple doesn't support music bought outside of ITunes. You have to import and then convert to whatever compression app that they use.
A:AnsweriTunes should synchronize your library to your iPod. When you connect your iPod to your computer that has the iTunes app so click the iPod icon. Once iTunes is opened and you attach the USB from the iPod to your computer, the icon appears. Click on the iPod icon to syn.