lost a whole drive of ....stuff after i reorganized all the said stuff into that drive. thankfully i got the other things out of that drive beforehand. but daaaayum mah years of stuff maan
i find that i never go back to those years of stuff .. except for photos
same...told my dad to throw out my notes from university...before it was hard to let go
there is sentimental value once you have built up years worth of stuff, no matter what kind of stuff it is 
digital hoarder? lol, i'm like that too, but never really felt too bad with very old stuff lost though
just purge everything and start over fresh~
i have mp3s from 1997 lol