Kevin is having issues with iTunes. It won't open at all. Leo says it should, and that isn't unusual. Sometimes .dll files get corrupted. Try uninstalling and reinstalling iTunes. Will that delete his music? Leo says no. It'll be safe. But Leo says that iTunes is an app that has never really worked well, and over time, it's gotten more ungainly and difficult to use. It really needs to be stripped down and built from the ground up. Alternatives include Double Twist. Media Monkey.
Charles has a thousand MP3s and he has multiple copies of all the songs, which is annoying. Leo says that in the iTunes settings, he can tell it to manage his music. But since he already has an iTunes folder with duplicates, Leo recommends taking it off his hard drive (to a thumb drive) and then restart iTunes and select the option to let iTunes manage his music. Then he won't have to deal with duplicates. iTunes is a terrible program for syncing music, especially in Windows.
Henry has a home theater system running iTunes for playing music and he wants to expand it to other rooms. But since Apple has discontinued the Airport, what can he do? Leo says that the good news is, there's a better way to do it. Apple has released the HomePod for that purpose, but Leo would wait since it's so new and early in its development. He recommends Sonos Connect. He can connect speakers to it, or he can buy Sonos speakers with the built-in connection. Then he can control it by phone or by Amazon Echo.
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.
Walt has a few hundred CDs and he'd like to rip them, put them on a music server, and then donate them. Leo recommends ripping in a lossless version called FLAC. FLAC is a great because if one needs to re-burn to a CD, they can. If using iTunes, he should use Apple's own lossless codec. Using a Mac that stays on all the time would work, but Leo recommends using a Network Attached Storage device and have that run as the music server. It can also do double duty backing up the network. Leo recommends the Synology brand.
Evelyn just got a new iPhone and wants to transfer all her settings and data from her old iPhone 5. Leo says the first thing she'll want to do is backup the old one in iTunes. Make sure to select encryption, because it won't backup her passwords without it. Then she can plug in her iPhone 8 and iTunes will then ask if she wants to restore. She can just select that, and then it'll backup her passwords, download the latest apps, and any other data she wants. Here's a support page from Apple on how to do it.
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.
Barb wants to give her old iPad to her granddaughter. She wants to know how she can transfer her old data onto her new iPad and then wipe the old one. Leo says to connect her iPad to her computer and fire up iTunes. Then she can run the backup and sync utility (it should run automatically). Then, she'll check the iPad icon on iTunes and see when it's synced. She can also check encryption. That will encrypt everything including passwords. She'll just give it a master password, and then it'll backup the iPad.
Ryan would like to learn to program so he can get a job coding. Leo says the first place to start is with the Stanford iOS course on iTunes. It will give him a step by step on how to code for an app. Leo also recommends a program called How to Design Programs (HTDP).