Mine's even uglier: Since disk storage grows much faster than my use of it, the last thing I do as I move to a new computer is to copy its entire hard disk to ~/archive/MachineName. (I do delete swap files since they're large on the newer images.) I (almost) never lose anything, but it's a bear to find things, and do I really need all those Windows files? On the other hand, I can easily recreate the entire working environment, OS, apps, and all this way, and that's saved my butt now a couple of times.

Fortunately, Win10 makes it easy to delete Recycle Bin and Downloads after N days, so at least some things are self-cleaning...