Depends on a lot of factors. The main reason to do it is that Jekyll - and their ilk - are so damn easy nowadays. And you can push the whole thing to an AWS ser

Depends on a lot of factors. The main reason to do it is that Jekyll - and their ilk - are so damn easy nowadays. And you can push the whole thing to an AWS server in one command with s3website. For $0/m, unless you're a big deal. You can even get free SSL with CloudFlare. Or you can just use GitHub Pages and circumvent that whole process. OTOH, if something like Medium weren't as bulky as it is and had more awesome CMS features like footnotes, I could totally understand somewhat-technical people sticking with them. It's less the self-hosting and -ownership that should be appealing, just how much easier it genuinely is to publish yourself for your own website compared to managing Medium.