I have my collection predominantly chaotically arranged (by choice; some years back I found anal perfectionism was adding a lot of discomfort to my life and tried to blot it out, pretty successfully; this was one weapon in the war). As a result, it often takes me a long time to find a recording in a room that is crammed with over 10,000 recordings now, two rows deep, etc.
I have indeed rebought a few cds because I couldn't find them. One I later discovered was in a friend's hands, one I finally relocated in my room, one I still now have only the new copy.
Them's the breaks, but overall I prefer the chaos I have. . . .