Paul has several interviews on his iPod of World War II vets and the iPods are dying, so he needs to get them off. He'll need a computer to do this. Paul will have to be careful not to erase the iPod, since that's the first thing iTunes will prompt him to do when he connects it. Then he can get a third party program that will get the files from the iPod.
David works for a zoo and wants to set up music that would play through the PA with announcements that would be timed throughout the day. He wants it to be automted. Leo says it's an easy thing to do. An iPod Touch or a Google Nexus 7 with an Alarm app could do it. Most alarm apps will allow him to create music playlists.
Leo says if the head unit in the car has bluetooth, that would be the easiest way. Dave says his car does not have bluetooth, though.
Another possibility is to connect the phone via USB instead. Or he could try getting an adapter, like this one from Belkin, to go from the iPod 30 pin connector to USB.
Leo says they're not doomed just yet, but that seems to be the trend. People interested in buying music players tend to go with smartphones and double up so they don't have to carry multiple devices. There's always a need for music players for people working out and hiking, though.