From reading some of the old posts in the UserVoice thread states:
There are a quite a few complications as related to licensing, partitioning, and security issues with windows servers.
https://digitalocean.uservoice.com/forums/136585-digitalocean/suggestions/2536799-support-windows-server

@hansen Thanks for that share.

@FrostGamers, on top of what hansen said, Windows isn't the go to OS for website hosting. If you are more familiar with Windows, I'd suggest looking elsewhere or, you could learn Linux. :D