If some of your files date back to Windows 3.1 days of 7 digit number naming, you are really in trouble.
I suppose one thing you ought to do is go through these files, open them up using the appropriate filters and save them in current formats, in new locations and with new names, and should do this any time you access a file. That means designing a file storage system and naming system all of your own.
Agent Ransack sounds good.
I must say hat this is an unpleasant thread to read.
I am concious that my hard drive is filling up and the external hard drive is a pain to use as a back up.
I have been using Easeus partion master to expand my C drive to give me more space (I don't use the d: drive for other than its original use so it has lots of unused wasted space).
I also used duplicate cleaner to rid my files of multiple copies (which doesn't rely on the file name but identifies duplicates more intelligently than that).
But still I have amassed lots of files on the hard drive and I hate to think of all those back up CDs with old Windows formats that windows won't open any more.
Some files it has been easier to find again via Google than on my own drive which has been one cause of so many duplicates.
And that is part of the trouble.
I once, mistakenly, simply bookmarked useful files found on the internet only to have a huge bookmark list and then to find far too many bookmarks were coming up with "file not found".
Plus searching for the original files again is frustrating. Google doesn't seem to search as well as it ince did or perhaps it seraches in a different manner today.
Saving the files is preferable but how should I save them? using the original file names or my own? And that leads to its own problems.
I sometimes think I was better with piles of paper copies in no particular order but which, somehow, the brain can navigate and search more efficiently (or more successfully) than going through My Documents.
JMW