As someone who it utterly sick of windows and recently had to suffer through the install procedure (override boot, select correct drive with different ordering, wait, date and time, no online account, yes I’m sure, YEs I’m Certain, beft friend Washington, mother’s maiden name Washington, pets name Washington, mute Cortana, wait for the ted dialogue to finish anyway, no Cortana, no telemetry 1, no telemetry 2, no telemetry 3, no telemetry 4, some telemetry {best choice before in os settings available on enterprise only}, wait for full screen notification to promise great things, remove bloat from start bar like news search etc, mdl scripts to restore basic functionality if using enterprise, install Firefox, install GPU drivers, actually go to a website to download and install software…) …* catches breath *…through the install procedure, If you are already familiar with windows and your desired server software is available for it, then you are probably better off sticking with it and getting it running. You may or may not be better off with Linux down the line but you can use another computer or virtual machine to test if it is worth learning. I highly recommend just debian for a server over ubuntu and if you need a desktop interface lmde. There may be “better” options but I don’t think they justify the learning curve if you haven’t been on Linux since the days of Intel selling slot loading CPUs.

Also when installing any operating system I recommend pulling the power from any important hard drives first. Windows in particular is very vague about which drive is which during installation, but when not used to it the Linux partition editors are quite different and potentially overwhelming