I have little experience with windows (web)servers and more with linux.
I have no idea why someone would want to set-up or manage a windows server. It's just pain if you previously did it with linux. Everything sucks. Where to find log messages, how to upgrade a php version and get that used by the webserver, backup, maintenance, how to write short and useful scripts for maintenance, the mixture of config files and lack thereof, and it needs double the resources.
I wouldn't do it in my spare time. I'd rather work on a way to get that OS in that VPS replaced... (My personal oppinion.)