What I found is I had back ups of back ups of the things I actually cared about and the things I lost I hadn't truly looked at in a long time. A lot of the music I hadn't listened to in years.
I have found that I can fit on small SSD drives and as a result of the things I do wish I hadn't lost, I'm just keeping up with the practice of keeping multiple back ups.
TL:DR: I have made an effort to keep a smaller data footprint instead of hoarding.