This is a great example of how much of a hassle the 8.3 name can be. Well, it’s really only a hassle if you want to describe the image using 8 characters.

I don’t have time to create an index or a database for my photos right now, so I’ve loosened up my own file naming.

I still put the year first, but now I use the entire year, plus “ca” for circa if it’s a guess. Then name(s) and sometimes a brief note about the occasion. It’s not perfect, but it’s doable and it works for me. Your mileage may vary, as they say.