How to transfer files after booting from external drive?

My fathers MB Air has been failing to boot, most likely due to lack of space on hard drive. I've come to the conclusion seeing as how its a 2014 model and he has 6 GB's of free space on his main dirve. I've managed to boot his MB Air from an external drive and now I need to know how to transfer his files to the external hard drive from the internal hard drive, while of course running on the external device. I apologise if this made no sense; trying my best here. If there is any more information required to answer my question please don't hesitate.

There are two backups to be concerned about. Your iOS devices can backup your App purchases to the computer (that can get big fast!) and it can also backup personal settings. Personal settings can be backed up to your iCloud account and Apple provides 5GB free space which is just enough to back up two devices. I suggest the personal data (basically how you have your iOS device configured) be backed up to the cloud rather than the computer. This will free up about 5GB. Once this has been done, open iTunes, select preferences, click on the Devices tab and you'll see the stored backups (if any). Delete each one.
The backed up apps are stored in the iTunes folder. Inside the music folder you'll find a folder labeled Mobile Applications. Good news: you can delete this folder (mostly) safely because it costs nothing to redownload apps if needed. Bad news: if the app is removed from the App store it can't be downloaded again. This has never affected me but it is a potential problem. My solution is that I don't backup my apps to the computer. In the rare event that I need to wipe my iOS device and restore it I've found that downloading the Apps again (which is done automatically for you, no need to remember what you had) takes no longer than restoring them from the computer's hard drive.

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