One of the things we ended up talking about was physical photographs and how our families had developed a natural curation and annotation system. "Keepers" get sorted and labeled on the back with names, dates, brief notes, etc. and placed in albums. There were a bore when we were younger, but now we appreciate having some long-lasting artifacts of our families' lives and history. This is a nice thing and differs in importance to my every day interaction with personal media.
If I had the talent, I would make a small journaling tool for myself. All I would ask it to do is remind me once a week to select a favorite photograph and make a brief note about who's in it and why it's important. Really, just 30 second a week. Then, one a year a nice, archivally printed photo album would show up on my doorstep with all of these photographs arranged and discretely tagged with names, dates, and notes. That's it.