Will I keep files on another hard drive when upgrading to windows 8.1?
No. When you install windows it will ask you what hard drive you want to install it to. And if you're really skeptical on it, just unplug the hard drive before you install windows, that way there's no way the data will be deleted.
Also, I'm not with windows 7 but if you purchase windows 8 you'll get a free upgrade to 10 when it's released...so do what you wanna do.
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