Scott has an iPad Mini 2 with thousands of pictures on it. But when he plugs it into iTunes, it won't back them up. Leo says that backing up the iPad should have moved over all the photos. So if it didn't, that's a concern. iTunes should back up everything, then he should be able to restore it all to a new iPad.
Rock On recently had a contact mysteriously show up in her contacts list on her new Android phone. Leo suspects that it's through Google Contacts. If she deletes them from Google contacts, it'll be synced and deleted from her phone as well. It could also be Facebook that's populating her contacts as well. Once that's deleted, it shouldn't come back. She also may want to check with her carrier to see if they're syncing her contacts as well.
Richard can't do a backup -- it just stops. Leo suggests running "ChkDisk" to see that everything is OK with the data. But Leo also says that Microsoft's backup program isn't all that great because it dumps all of the data into one giant furball of 1s and 0s. That means it has a single point of failure. And there's no way to know if it has it all of the data or not.
Debbie has an old 2007 MacBook. She can't plug her iPhone to it and transfer her data. iPhoto keeps quitting on her. Leo says that she can turn on Wi-Fi syncing on the phone and use that option. It's slower, but it will work without crashing. iCloud Syncing is also a good option. Then she can sync it without even running iPhoto.
Diana bought a new Apple iPhone 5. The Apple store employee merged her contacts, but every contact in her phone was from iCloud and not her personal contacts. Leo says that's probably true. He assumed that Diana's phone was backed up, and it wasn't. Going forward, Diana should continue to backup to iCloud so if she loses her phone, she'll still have her contacts. She should just clean it up first. Then back up her contacts to the Cloud and have it continue to backup regularly.
Eric is having trouble syncing his wife's Fitbit with her phone. Leo says that the Fitbit will use Bluetooth to sync to the phone with the Fitbit app. Eric will have to pair it. Then she can use her cellular data to upload her Fitbit data to her account. The Fitbit doesn't need Wi-Fi to work -- it just needs Bluetooth to connect to the phone.
Rick is having trouble getting his iCloud Drive to sync. It just keeps searching. Leo says that Apple historically has had issues with its network and with sync, and nobody really knows why. That's a good reason to not only rely on it for backup. That's why Leo has third party solutions like the File Transporter.
Marsha would like to sync Outlook with Google Calendar so she can sync with her Android phone. Leo says that Google used to have AppSync, but they discontinued it. There are third party apps Marsha could use though: