That being said, we're all getting older every year (don't I know it), and so does the server software. While I could just bluntly try and upgrade it and bring all the old gremlins forward with it, I prefer to get a completely new server and move everything there into a fresh system every ~two versions of the game

I'd like to do this after the current running season, as far as I know there is still one going on.
There is very slight possibility of things going wrong and it taking a lot longer than anticipated (days instead of hours), so that is why I'd like to do it during off season.
No data or history should be lost as this has been done once before in 2019.
I do not want to disturb the hard work that has been going on, so let me know if there are some things I should take a note.
At the moment this is in planning phase, as usual things will happen in chaotic time table with very little planning. The blood bowl way.