Do you mind if I ask what format you've settled on? Having a system evolve over multiple generations means you must have pruned out all the bad ways to do it.
I've got this vision of a Neal Stephenson story which will never be written about a family in the 22nd century that has kept all their personal contacts in Git for over 100 years ...
Grandpa was an early adopter of computers due to his work in cryptography, which started even before WWII. He wrote his files mostly in WordStar, and a few other formats that are still readable. Most of these are on a drive and on 5.25 and 3.5 inch floppy disks. Dad uses KEDIT, and now Notepad++, probably because KEDIT was popular in Princeton at the time. I think John McPhee still uses KEDIT. I use plain text files and HTML.
