With regards to Jekyll. I'm not familiar with the Ruby ecosystem Every time I try to upgrade either Ruby or Jekyll on my machine I have to trouble shoot for hours. Really hampering my desire to update the blog. There are also extremely weird restrictions. For example, accidentally adding tab-characters completely breaks config files and an overview of posts can only be generated on a file called index.html.

@roytries I can recommend https://gohugo.io if you're looking for a jekyll replacement. I switched my Octopress site (also Jekyll based) after that project was no longer maintained and it became an unsortable dependency hell. There are plugins for jekyll compatibility, so switching is fairly simple. I managed to transform my theme within a day and retained most functionality, including URL/slug layout. Fast & easy!