I have tried to do it a few times, and eventually just gave up. Carrying forward bad naming decisions from the past, is tremendous effort. When cleaning up the house, I also don't leave around sticky notes at the places where I removed documents from.
On top of this:
- When using static site generators, it's not even possible to do 301 redirects (you would have to ugly slow JS version).
- It does not help if you don't own the old DNS name anymore.