I’m in a similar boat as you and my current plan is to switch to PopOS. They are Ubuntu/Debian based so you will be familiar with it, and they also are a distro that is more focused on gaming, so you will have an easier time with video card drivers.

My family relies on OCR to find documents anyways. So of I’m gone, they could just upload it to onedrive or something similar and search that way

It only does a backup of media folder in paperless, so its not organizes in a meaningful way. But I never organize my documents anyways.

I do it because I like having full control over my data and services. Nobody can take it away from me or change the terms in which its provided.

Every couple months when I do server patching I run a script that downloads our immich library, paperless documents and bitwarden backups to an external hard drive. Then I put the drive in my gun safe. She knows where it is. After that she is on her own. Everything else isn’t important and she will be just fine.