I’ve been using Windows 8 on the server for a while now. It worked fine for what we needed. I didn’t care for the setup much, but I didn’t need to mess with it much either, so I got along fine with it overall.
But then I tried to host a website on it…
I grabbed XAMPP for Windows and got to work migrating my website over. That wasn’t really an issue. However, the way I generate blog posts for Jekyll involves running a simple script that I wrote that moves some files around and invokes jekyll, a Ruby gem…
Getting Ruby and the Jekyll gem installed on the server was OK, but it’s easier on OS X or Linux. Still, all I had to do now was get my script to work remotely, since I generally write my blog posts away from home. Unfortunately, I never got this to work due to permissions issues related to how Cygwin & OpenSSH authenticated with public key auth on Windows. Back to the drawing board.
I weighed my options. I needed iTunes for Home Sharing, some kind of web server, some kind of file sharing that works with OS X and Windows, an easy-to-configure VPN server, and a universal remote backup solution. Linux could do everything except iTunes, and Windows was out, which left me with OS X…except I wasn’t about to replace my server hardware with a brand new computer.
There was only one thing left to do.