Samba is amazing, Windows server is a lot less so. The problem with Windows server is that it takes tons of steps to do basic things. On Samba I had Samba tool and it was very nice and friendly. On Windows server you have a ton of different management panels.
If there was a way I could hold off I would but due to changing requirements I didn’t have much of a choice. (We needed Windows Server bare metal and I was not about to go and buy another machine.)
I’m sorry for your loss. I’ve done administration of both, and I loathe working with Windows.
Funny how the so called “off brand” solution is so much simpler.