Linux
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I think you're starting too big, to use your phrase.
Get used to the basics first: what's different (to whatever you're running now), what's the same. They Linux distributions almost all have GUIs (KDE, GNOME are the main ones but there are many others).
Run a live USB version from a usb stick to get used to it until you have the confidence to install it on an old pc. Personally I do not recommend dual booting; data gets lost that way. Install it on an old pc and learn how to restore your backups to a Linux filesystem (not the fs of what you're used to on Linux platform). I write that because you said that want to end up with a Linux server.
Choose one of the top few from distrowatch.com/
Your aim is to understand what's going on under neither the GUI; how permissions work.
I started by installing a VoIP product into a VM on Windows 2000, but there are better ways now.
Good luck. You shouldn't find it that difficult.