I can't imagine a guy with 500G of personal files. It must take a month just to read the titles of his various files.
Off-topic but I thought I'd share how easy it is to accumulate 500G of personal data very quickly as I'm well on my way there: Digital photography. If you're a serious amateur and shoot in RAW format with a 14MP or so digital SLR, each photo can be around 15meg.
I can take between 250 and 400 photos on a night out with friends, still having a blast at the time, and these all add up very quickly. Throw in photos of family, holidays and such-like and you're running into hundreds of gigs of photos very quickly; I've got just over 200G of photos after having my camera for around 10 months. Software like Lightroom, iPhoto or Aperture makes organising and searching them very quick and easy, too.
The only things I'd be mortified about losing are my photos. It'd be a pain in the ass but code can be rewritten (probably quicker second time round, too). Mail is stored on the server. I can't ever again recreate the moment I pressed the shutter on the tens of thousands of photos I have, and I still haven't found a reliable way to back them all up frequently either.
G.
"You can have my Unix system when you pry it from my cold, dead fingers." -- Cal Keegan