I am fairly meticuluous about naming and labeling all the digital photos I take and store in iPhoto. I continually try to keep up with giving each photo a title and listing who is in it. Currently, all of my 15,000+ photos in my library have been named, although about 3,000 are imported scanned images with little more than the filename associated with the photo.
It's these 3,000 images that have been my pet project recently. I've been trying to associate dates with them, with the ultimate goal of having all my photos identified with dates. Sometimes, this is straightforward to do, as in the case of my Hawaii photos. My detailed web journal and photo naming convention made it almost a mechanical task to assign a date to these photos. I set the time on them arbitrarily just to ensure that they stayed in their correct sequence.
Most of the other older photos, though, are harder to pin down. If the photo is of an event (Christmas, graduation, etc.), I might be able to do it, but that is a small minority. For the majority, I'm hoping I can pin it down to a month and year, but sometimes even a year might be tricky. I'm sure this will keep me occupied for a while.
But even doing this much in iPhoto is tricky, since iPhoto does not support partial dates. You can only specify an exact date and time for every photo - no more, no less. I could simply set the date to be the first of the year for those pictures that I can determine the year only, but then how do I differentiate pictures like that from the ones actually taken on January 1 of that year?
My current workaround is to use iPhoto keywords to identify those types of situations. I have defined two keywords: "year only" and "month-year only" that I associate with photos for which I could only determine a year or a month and year, respectively. This seems to work pretty well: my photos stay in chronological order (mostly) while still allowing me to see which dates are true dates and which ones are approximations.
My iPhoto fastidiousness also means that I'm really eager to get the new version of iLife. iLife '09 comes with enhancements to iPhoto that identifies faces in pictures and tracks locations of where pictures were taken. Since I have a large set of pictures already labeled with people in them, it should be straightforward to flesh-out the built-in Faces grouping in the new iPhoto based on my existing data.
No tracking "places" in iPhoto is something I've not done yet. That will be another fun iPhoto project for me to tackle sometime soon...