Tony has used up 4.9GB of his iCloud storage and he doesn't know how he's used all that. Leo says it's likely his phone backup. He can go to iCloud.com and login and see what's there. Chances are, if it isn't a phone backup, then it's likely all of his photos, which get automatically uploaded to the cloud. But he's wondering why it saves all his text messages and deleted email. Leo says he can probably change the mail settings to use less space. He should look in his email settings and choose things like "don't save attachments", etc.
Larry's computer died and he has to buy a new computer. How can he move data from his old computer to his new computer when the old computer is dead? Leo says to go to Newertech.com and pick up their Universal Drive Adapter. This will allow Larry to take the old drive out of the computer and connect it to his new computer. He can open it as a drive on his new computer and just copy the missing data over. But if the drive isn't functioning any longer, he could be out of luck.
Jim is having problems with Windows recognizing his external USB drive. But his image catalog says his images are there. Leo says that many photo gallery apps keep a thumbnail for fast referral. So it could have the thumbnail, but not see the original image, if the drive is disconnected or lost. Leo also says that his external drive could be getting flakey. He should get a backup drive and make a copy of his photos. He should save them online, too. Three copies, on two formats, with one off-site. The good news is that hard drives are cheap now. He can get a 1 TB drive for under $100.
Charles wants to know the best way to set up Time Machine on his Mac with macOS Mojave. Leo says that in the new OS, there is a new APFS file system, and there have been backup issues with Time Machine and others. He may need to use an external drive formatted with the old HFS file system. That will insure that if his internal drive dies, his backup is secure. Leo also recommends not using Time Machine as his primary backup system. He should make an image backup with SuperDuper.
Barbara would like to update to macOS High Sierra, but she thinks that she can't update it because she hasn't updated in a long time. Leo says you can. The way you can do it is to go to the last version your computer can handle directly. If that's macOS High Sierra, then just go to the app store download it and install. If you're getting notifications, then you're golden. It'll take awhile though.
Tim uses Time Machine for his backup, but the backup fails intermittently. His Synology NAS is citing improper credentials as the cause. Leo says that encryption certificates need to be renewed from time to time, and if he's encrypting his data on backup, that could be the issue.
There is a post on Synology forums about this: Time Machine, Making it Work. Learn from my Suffering. There are some steps that can help.
Paul had a Dell XPS computer, then he got an iMac running Boot Camp. He hasn't been backing up since December. He changed the file structure when he moved to the new computer, and now his backups are duplicates instead of a select backup folder. Leo says he can tell his operating system where his home folder is in the partition. Once he's done that, he can delete the duplicates.
John is frustrated that he can't delete the pictures on his phone without deleting them from iCloud. Leo says that if he selects "optimize phone storage" in settings, it will delete it on the phone without deleting it on iCloud. But he'll have to select "Keep Originals" on his Mac so it doesn't delete there.
Bonnie bought a new computer and plugged in her external hard drive. She can see the data on her old computer, but she can't read it on her new computer. Leo has a hunch that her WD Passport runs a proprietary utility that encrypts her data to protect it. She probably will need to install that same software on the new computer in order to see the data.
Manny wants to store his photos in the cloud, but he wants to have a better quality image stored locally. Leo says that iCloud always keeps the higher quality image in the cloud. In Google Photos, he can turn off "optimize photos" and it will keep the higher quality locally as well. But Leo says he really won't see the difference.