[ciroduran]

I recently had to nuke the Linux environment where I had my Jekyll environment finely tuned (Ran it on Debian WSL). Then I realised I had to reinstall Ruby, but the current Jekyll version (or the gems I use) uses a version that needs to lock OpenSSL at a certain version because of some breaking changes. Tried to lock the version in Debian and I was having a really hard time.

Then I realised I just could grab the latest Jekyll image from Docker hub and build my website with it. And just like that I was able to build my website without dealing with any ridiculous dependency.

So yes, you should write your own static site generator because it might be a tad easier than trying to install from scratch the dependencies of whatever generator you have chosen.

[HuwFulcher]

If you used Go (or something equivalent) couldn’t you bundle it into a binary and then it can be more portable?

[ciroduran]

It's good to have a binary that you can run, but you'd still have to deal with Go dependencies at build-time, and Go dependencies sometimes can go sideways as well (probably not as bad as Ruby, though)

[HuwFulcher]

Yes, build time will still be an issue. Hopefully if you get to a point where you’re “happy” with the binary you can avoid build issues for a while