A big differentiator in how you might want to tackle this depends on one question, are you planning on getting into Linux systems administration, like for work? Because if you actually really want low level Linux skills then that’s a whole slew of things you’ll need to learn from scratch. And it’s not just your Windows-only experience that’s holding you back, managing a server is different from managing your desktop.

But if you’re not really interested in working in IT or all you really want to learn how to self host, you’re probably better off with an appliance, like UnRAID. These OSs abstract away much of the low level stuff so you don’t have to worry about it. Not the best way to learn how Linux works really well, but the easiest way to manage your self hosted environment.