Todd has bought a music track from iTunes and has to edit it and convert it to MP3. Leo says that he can go into Garage Band and edit it. If it has copy protection, pick it up from another source like Amazon Music. Then import into Garage Band.
Steve is concerned that replacing iTunes with a series of apps in macOS Catalina will cause Windows Users to not be able to sync. Leo says that while Apple will be shutting down iTunes downloads, he doesn't really see them coming out and stopping sync within iTunes for Windows users. In the mac, Sync is now done with macOS through the Finder. So there will likely be a similar solution for Windows users. But the trend now is that people are streaming now. Download & sync is being used less and less. But if it does, Leo recommends DoubleTwist.
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
Ed has a 13" MacBook Pro and after moving his music over using iTunes, he now has duplicate files and they won't play anything. Leo says what you want to do is import the music and not make a copy of it. That will tell iTunes where to go to access the music. So now, Ed will need to get a dedupe app to remove the duplications. Or you can search for everything that includes "copy 1" and "copy 2" and delete them. Then reimport them without "making a copy" enabled. That will reindex iTunes, pointing to where the files live on your external drive.
Rob wants to know what he can use now that iTunes is going away. Leo says it isn't going away; it's just being divided into Music, TV, and Photos. The sync is being incorporated into your OS now, which Leo says is the best part of the whole idea. But an alternative is VOX on the Mac. Leo says it's a third-party music player that plays high-resolution music.
Octavio wants to make a switch to iOS, but he wants to know how he can do backup while on the road and not use iTunes? He wants to also backup his Windows machine with the same option. Leo says that if you want a "trust no one cloud backup" then there really isn't going to be a solution. But a local backup is your best bet for that, and that means a NAS (network-attached storage). Leo likes Synology. It'll backup every machine, except Octavio's iPad. Your only option there is to iCloud directly or through iTunes.
Richard is visually impaired and has been listening to an audio book he converted from iTunes. But his phone won't play it. Leo says that audio books usually have an M4B standard to provide for bookmarking, and many audio players don't support it. It also gave him multiple copies of it. How can he bypass iTunes and play it? Leo says Richard could try iBooks. It will not only play audio books, but it can sync. But Richard says iBooks will only support purchased items. Leo says it will.
Jon complains that U2 will start playing when he puts down his phone and gets into the car. It's very annoying. Leo suspects that it's the free U2 album that Apple gave to everyone a few years ago. It's called Songs of Innocence and it's probably in iCloud. Apple created a special tool to delete it, he can get it here. But the larger issue is that when he gets rid of it, his Bluetooth audio in his car will just play something else.
Phil says that people also need to have a real radio in their disaster kits as well, so you can get emergency information in the case of a natural disaster.