Does this “obviously” have to use AI? I can see a tool that sorts files into folders based on file extensions, modification dates and/or metadata could get the work done.
And if organising files by content (e.g. “my zoo trip”, “meetings with Xenia”) is that important, doing it manually seems like a better idea because accuracy is presumably important.
I don’t really see the distro hopping argument either. Even if you don’t share your home directory between installs, presumably you copy over your files as directories rather than individually pouring them into one super folder?