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Good question.
A GUI will be easier to get into - you can use a gui file browser app to learn the layout of the file system, you can use a GUI text editor to change config files, that sort of thing. It'll mean you can do a few basic things intuitively which will be less intimidating. So from a maintaining momentum and morale point of view it might be best to have a GUI initially even though you have to learn all the cli stuff eventually anyway and you'll most likely be running a headless server on real hardware eventually.
Alright, thank you. This will be the first step. Debian in a VM, full GUI to learn all the basics.
Genuinely, I really appreciate the guidance here, I really want to learn to be as independent as possible tech wise and I’m really excited to get started with this.