Probably should refrain from commenting, but ... that's not my nature.
Think about this a minute ... the latest 3.2 of Moodle ... to get Search requires an Apache extension ... Solr which requires the installation of JRE. (is there a solr extension for IIS?)
There is also the issue you are having now with Unoconv (will admit that many seem to have issues with this regardless of platform, but ...). Unoconv is really a python script that interfaces into headless libreoffice. (BTW, from what I've read about office suites lately, OpenOffice seems to have stagnated but not so with LibreOffice).
None of the above is native to Windows.
Note that unoconv is 'faceless' (being a script) as is the process used to do doc conversions ... libreoffice in a headless mode), the JRE/solr thing does have a web based interface into it's config which probably should NOT be accessible cept to those who admin the server/service.
In working with the MySQL DB most often is recommended PHPMyAdmin ... a php based app. Ok, running MSSQL ... is there a php based or any based web app for remotely admin?
Just maintaining (updates and upgrading) a Moodle site via FTP is, IMHO, antiquated ... Moodle has yet a way to update or upgrade a Moodle from within Moodle Admin itself (Worpress, Joomla, and other very popular open sourced web based apps do). By far the easiest way to maintain (acquire updates and/or upgrades) is via git. Git is also not native to Windows.
And a real bottom question ... what does a GUI interface into a server that runs software that for the most part is 'faceless', really do for the server Admin?
Now in defense of Windows ... Microsoft is coming around ... no longer the 300 pound gorilla they used to be. They are developing/have developed a Linux of their own ... to help with the Guest OS's on Azure (will never release that to the public). There's additional software one can install now that enables the server admin to run bash shell scripts .... etc. BUT, is all that compatible with the version of Windows you are running right now (this is not to mention the licensing fees [Microsoft Tax]).
In certain areas, don't think one can beat a Windows server ... LDAP comes to mind here.
But for open sourced apps such as a Moodle?
Analogy (poor one at that) ... if I had a Mercedes don't think I'd be taking it to the local Joe's Mechanic shop unless there were some mechanics that had Mercedes training/equipment/parts, etc.
My 2 'sense' ... nope, spelled it right! ;)
'spirit of sharing', Ken