Van has an old iPod Nano and wants to back up the media from it. iTunes doesn't work because while it sees the Nano, it's grayed out. So you can't really do anything with it. Leo recommends iMazing. It will work with any "i device." They have a free trial before you buy it. Another option is the Wondershare Doctor Phone. It specifically says it supports the iPod Nano.
If you have an old iPod and there are music files that haven't been transferred from computer to computer throughout the years, it is time to back up that library as soon as you can. If you use a Mac, there's an app called Senuti (iTunes backward!) that can help with the process. For Windows users, try YamiPod. At the very least, back up the iPod onto your computer with iTunes via the "Back Up Now" function. Don't lose those years of music tracks!
Thomas has an old iPod and the battery is starting to die out. Can he get the battery replaced? Leo says that if Apple is no longer replacing the battery, check out iFixit or a local place that could do it. But the reality is, a replacement may not be all that helpful because people are now using their mobile phones for playing music, and any modern phone or an older phone people no longer use will act as an iPod as well. Leo recommends copying all music onto a PC first. iTunes would work, but it usually doesn't get everything.
To manage music on your iPod, you will need to use iTunes (even on a Windows PC). Use the "sync" feature to only sync "checked" songs, as unchecked songs in the music library can be removed. Make sure there are copies of each of your music files on your computer. In the library. you can sort tracks by artist, album, and custom playlists. If you uncheck all, then you can basically clear your iPod of space and then pick what you want to add anew.
Carol has an iPod that's getting too full and wants to know how to get everything off it and allow you to put other music on it. Leo suggests using iTunes and it's sync feature. Set it up to only sync checked items. Anything that isn't checked will be removed. Some items, though, won't get unchecked in her iPod. Leo says that's not where you uncheck them. You uncheck them in iTunes. Here's how - https://support.apple.com/en-us/HT201593
Don is interested in Personal Locator Beacons and Wireless Trail Cameras. Leo says that while he has no experience with PLBs, he does know that there are competing networks with various benefits. Here's a great article on the difference between PLBs and Satellite Messengers.
Travis works out a lot and would like to grab 30 second snippets to work out by. Is there an app or function that will do that? Leo says that there is no function on the iPhone or iPod, but iOS12 has a feature called "Shortcuts," so he may be able to create a shortcut to play just 30 seconds of a song. Shortcuts works by daisy chaining tasks from apps. Some headphones have a skip button, where he'd tap the button twice to skip.
Stacey made a one letter error setting up her iPod and she can't download any music on it. She went to the Apple store and the Genius punted and said to call Apple Care. Leo says that the music industry insisted on using a single iTunes account authorized to an Apple account. Stacey should be able to authorize the iPod using her Apple account. If she resets the iPod through iTunes, she should be able to set it up as a new device.
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.