I'm glad to hear I'm not the only one who constantly ran into issues with Jekyll. The last time was particularly bad. Even after removing my whole Ruby environment and setting things up from scratch I couldn't get things running again due to mysterious compilation issues so I eventually gave up.

Luckily my use case is super basic (just a personal website with a bunch of my projects), so a good solution for me was to switch to a custom Python script that pulls in liquid and markdown packages and has just enough features I need to generate my site.