The original manual for my copy of Panzer Dragoon Saga was dropped in a puddle of water by the person who gave it to me. It was a former friend who basically let me have all of his Saturn games after he got a Dreamcast (he didn't really care that much about his older games after he got a new system), and of all of the games that he could have dropped the manual for, he drops the ones for the Panzer Dragoon Saga. It took me more than 10 years to find a cheap replacement.
I also lost more than half of my pre-millennium collection in a house fire, and the majority of the rest of the pre-millennium stuff that was in storage at my mom's place in Hurricane Katrina. I do have a few game cases that survive both tragedies which are stained with soot from the fire though. I've since replaced most of them as I've some across duplicates here and there in game lots over the years, but I still keep the stained ones as mementos.
I don't even want to think about games and consoles that I've acquired and discovered dead (or in some cases LIVING) roaches in back in the day. Urgh....Jesus! One of the best things about living in the Mid-West (coming from the deep South) is that I haven't seen a roach in some 15+ years.