I have been on and off Linux basically since it first came out in the 90's (rather in the mid-late 90's in my case). I remember the day the computer magazine I used to read every week came with the Red Hat cd and getting together with my friends to install it...
I can't talk as far as servers go, only as a client-user, so good if Windows Server works. As a "normie" client-user (student, then non-tech work), Linux simply wouldn't be sustainable, so I always ended up being dragged back to MicroShaft's malware. And it would soon get worse the following years, by an order of magnitude, with the advent of Evil Corp (Google + Apple).
I think that the situation has changed dramatically now and that Linux is finally retail/normie ready. And the advantages are simply enormous, but more importantly, are becoming even greater imminently. We just can't surrender and take all this fucking spyware and abuse that Evil Corp intends to push down our throats anymore.
BTW, you don't need to pay anybody to "teach you Linux".
Just make a bootable USB of a friendly distribution like Linux Mint or Ubuntu, and play with it. Absolutely everything can be very easily found online, explained step by step in great depth.
Then the next step is to make a persistent install, just a dual boot living next to your Windows install, and use both normally and see how you like it. You will soon find you really don't need Windows at all to do anything you want to do. Even run Windows applications.
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