Lori is having a problem with her iPad 2. She syncs it over Wi-Fi, but lately when she tries to plug it in to her PC, it won't let her sync. It just requests to restore to a backup. Jason says that the PC is looking at the iPad as if it's a new one and can't identify it. Updating iTunes on the PC and iOS on the iPad could help. The iPad 2 doesn't support iOS 10, though. She may be at the end of the line there. If it offers to set it up as a new iPad, that may be OK, as it pulls the data off the iPad and syncs it. That can be scary, so Lori should have iCloud backup enabled.
John wants to know if he can get an older iTunes Pro 7 version to work on his MacBook Pro. It's easier to use. Leo says that iTunes has become awful and it really needs to be redone from the ground up. It's just plain unintuitive and broken. Apple does offer older versions at support.apple.com/downloads/itunes. The oldest he can get is iTunes 9.2.1, though.
Sam used to have Windows Home Server, but since Microsoft killed it, he's been looking for an alternative and found Drive Bender. It uses a technique called Drive Pooling and it enables him to hotswap drives and rebuild them so he doesn't lose data when a drive fails.
Avatar is having trouble getting his pictures from his iTunes backup. Leo says that iTunes is a really old program now and Apple really needs to completely rewrite it. There is a backup icon that will enable him to back it up. On a Mac, iTunes will backup everything. On Windows, it backs the images up to "My Pictures" when connecting the phone. Avatar will need a photos app to do what he wants iTunes to do.
Scott is using iTunes on his iMac and he's trying to move his music to his new Samsung device. Leo says that if the music is copy protected, he'll have an issue. If it isn't, then he can easily use a product like DoubleTwist to get his music on it. For copy protected music, Leo advises getting an iTunes Match subscription. It's $25 and it will replace the copy protected music with DRM free music.
Ian is trying to back up his iTunes folder with a flash drive, but the drive turned out to be too small. How can he tell how large his library is? Leo says to open the iTunes program and look at the bottom of the window. That will give him a general idea of how big the media folder is and how much music it contains. He can also just right click on his iTunes Media folder and select "Get Info."
Dave has a lot of songs that had been downloaded from Napster a long time ago, and all of the cuts have been put on a disc at least once. After doing some rearranging, when he tries to burn certain cuts to a disc, he gets a warning message that says he can't rip or burn them because he doesn't have a license. These songs were all paid for, though. The files were on a data disc, and some of the songs are WMA and some are MP3. If he were to make an audio CD, all the songs would be converted into a special format that could be played back in regular CD players.
William uses an iPhone 3GS and an iPod and wants to upgrade to an Android phone. Leo says that if he wants to move from an iPod to an iPhone, that's really easy via iTunes. For music he bought awhile ago through iTunes, however, he can't move that to Android. He'll have to strip all the DRM out by paying $25 for iTunes Match. Then he can download all the music back from Match with DRM free versions, and with better quality sound. There are some apps that will enable him to move his music from the iPhone to Android.
Dennis got an iPhone 6s Plus a few months ago and he can't seem stop the storage from filling up his phone. Leo says that the iPhone caches a lot of data. If he plugs it into his computer, he can take a look at it in iTunes. It will show him a graphical representation of the space used in "other." The only real way to clean it up is to backup the iPhone, erase it, and then restore it. That will get rid of all the cached stuff. He can go into Settings > General > Storage and Usage, and clear everything out piece by piece.
Connie has her iTunes music on an external hard drive and once she's copied it over to the computer, she unplugs it and the music disappears. Leo says that's a preference issue in iTunes. She'll want to look where her iTunes Media folder is in the preference settings. iTunes may be looking for it in the external location.