I only put our blog posts a couple times per year, but it seems that the Jekyll dependencies move beneath my feet and break routinely. This is especially a pain because Jekyll and homebrew are the only ruby projects I work with frequently, and so I'm always at a loss for how to fix things -- rbenv, updating gemfiles, do I need to gem or rake or bundler something, architecture-specific problems with C dependencies, yuck.
For now I just put everything into nix which seems ok, but I think I may make a third attempt at switching to Hugo soon, or maybe this, or maybe cobalt.