Chris has an old iPod Classic. But since his PC died, he needs to find a safe way to get his music off his iPod and back onto his new computer. Leo says that Apple doesn't let you do that because they're afraid of piracy. But there are third party options on both Apple and PC.
Paul has an iPod with some unreplaceable media on it. It won't let him charge anymore and he's afraid he's lost his media. Leo says it depends on how old it is. He should look on the back and see what the model number is. Chances are, the battery just doesn't hold a charge anymore. He may be able to replace the battery. Before he does that, though, he should try and get it powered up by connecting it to his computer. If it powers up, then he can get the data off with iTunes. If not, that model iPod has a spinning hard drive in it, so he could remove it.
Martin wants to know if he can still buy MP3 players. He wants to bring his music with him and doesn't want to stream it. He also doesn't have a lot of storage on his phone. Leo says that there are still some available, though the category is shrinking. SanDisk has the Clip, which has 16GB of space. It's around $30 and is very simple. Search Amazon and he'll find a lot of them, mostly Chinese made.
Jason has a Windows machine and an iPad Air. He syncs iTunes to it. His iPad is broken, though, and he wants to know if he can restore his iTunes to his PC. Jason says he can get his files off the iPad using Senuti. There's also TunesGo. It'll probably just pull the files off, meaning he may lose his playlists.
Char wants to take his old 60GB iPod and use it to copy files from his computer as a kind of hard drive backup. Leo says that when the ipod first came out, you could do that. But with newer models, Apple made it difficult to do this to prevent piracy. Char can do it, but he'll have file names that look different. Leo advises using Senuti.
Jay has an iPhone 5s and his new Mac doesn't recognize any photos from before he bought the 5S. Leo says that there are plenty of alternatives including Google+, Microsoft One Drive, DropBox (only 2GB), and Flickr. There's a ton of options and some are free.
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.
Dennis goes overseas a lot and listens to both audio books and podcasts. He has an audio library now of several hundred books. But recently he's been unable to transfer purchases from his iTunes account. It requires him to erase his iPod to transfer them. Leo says that's copy protection nonsense. One thing Dennis can do is download them again from Audible.