I know I struggle with this issue. That's why Tony Proctor's presentation regarding indexing off file names during last Monday's session of Monday's with Myrt proved intriguing. (Organizing More Resources)
Tony developed a simple program to attach a 'buddy file' to the image. As he was presenting, I kept thinking, about the time involved to add this information to each and every photograph.
Then, Hilary commented that she has been using Tony's program to attach transcriptions to a digital image. With the transcription attached to the image, I would be able to search my files for a member of an ancestor's FAN club and find records they were mentioned in. That makes it worth the time to learn how to do this.