- Layout & Routing - Having "special" pages is usually impossible with "structured" SSGs (like Hugo). For example, say you want a page that's your portfolio and only contains posts with x and y tags and you want it to look different than normal pages. Also see rss below. Or for example archives, where "/year" = "/year/index.html" but also "/year/month/" = "/year/month/index.html" and "/year/month/postname" = "year/month/postname.index.html".
- Sitemaps - I have videos on my blog and usually you want to add those to your sitemap properly. To do this I had to patch together a plugin to fetch the video info from the youtube api.
- Smart tags/embeds - Similarly I had to do something similar to fetch embeds from just the link like "[instagram]link[/instagram]". You have to do this with every provider you want, ugh, awful. Also means fighting the markdown converter you chose sometimes.
- Images - I run a blog with lots of images and different views of those images, so I need to have them all in at least thumbnail size and the regular size, sometimes the original as well, but not always. I used to batch convert new ones by hand but that was a pain. I eventually patched together a metalsmith plugin for this to automate the conversion of originals to "regular" (max post width) and thumbnails but it needs improvement. Edit: And I forgot, actually adding the correct attributes needed for lazy-loading, etc, to the image tags was also a pain.
- RSS, Most do not come equipped to handle rss, and available plugins are too simple (for routing that is, like having an rss feed per tag, per archive page, etc).
- Layout Language - Depends on the SSG, most allow choosing or these days are super flexible (e.g. Nuxt) but those that don't and just use one template language, argh! Template languages like handlebars are just not flexible enough. This was the easiest to fix though. I just use ejs now, basically allows any valid javascript, love it.