My CTF [0] that has been running for years will break and that's honestly my biggest concern. I have no clue how to even get it up and running again because I've mostly forgotten everything I learned to get it setup to begin with... I kept it out of my repo to prevent accidental spoilers if I ever made the repo public - though thinking back I really should have set up a CTF branch and just never published that branch. So lesson learned if I ever make another CTF: extensively document every single step for how to recreate and setup the game again.
Redeploying the site and even saving all the files uploaded to the site are both relatively trivial. The deploy is almost entirely automated and I can still login to my root user panel, download any uploaded files, and transfer them over to the newly deployed site - so I'm only experiencing minor data loss. (eg. the DateUploaded for files will be lost and I don't care enough to try and back that up to restore it)
Hopefully I do everything right and prevent link rot. Thankfully I'm the sole user of my file host so nobody else is losing any data.
[0] If anyone wants to become the 4th and probably final person to ever solve my CTF - you have just shy of 2 weeks before it breaks: https://nadyanay.me/ctf