My files are a mess, I try to structure them into folders with names that describe what they are in a recursive class break-down sense but later on I have trouble finding the fi
I came across this question while asking myself the same question about filesystem file tags. I then came across this application for Windows XP/Vista called TaggedFrog that may do the trick. Haven't tried it yet, but it looks promising.
Not looking forward to going through 1000s of files though! At any rate, I'll be forced to upgrade to Win7 at some point and can try its native tagging.