I’m curious, what big changes do you foresee having to make?
If you’re using a static site generator such as Jekyll, it would likely be trivial to run through all your markdown and import it into a DB or something like that if you move over to a CMS, but I actually don’t see that being likely judging by my personal experience.
I spent so many years building a blog. Once I switched over to Jekyll, I actually started writing and publishing content and I haven’t looked back.
Sounds pretty cool!