despite this will hijack the thread and you were asking Joost, I would like to give you an answer as well
I have build quite a bunch of Jekyll sites for myself. Unfortunately most of my customers were not appealed to use Jekyll. When I sold a website, people migrated to Wordpress.
At the moment I have 3 customers on Jekyll. We are using Forestry and CloudCannon, as they won't work with the CLI.
My customers were not happy with both of them.
One argument for my customers to pay less was the fact there is no CMS. No CMS = Cheaper, they say.
I also was looking at UpWork if there are Jekyll websites asked. There are a few, but most of them is like "please convert WordPress to Jekyll, I give you 100$".
Maybe Joost is saying differently, but I don't believe one can make a living as a Jekyll expert.
Me asking for help is pretty much an exception. I code myself, so normally I would code my websites myself too.
You may proof me wrong!