Picasa does a pretty decent job of photo sorting. You can check it out. It’s free, so you can use it and just uninstall it if you don’t like it.

Apple iPhoto (Mac Only, part of iLife, $79) – iPhoto lets you sort your photos a lot like iTunes will sort your music. Everything is in a library, but you can put a photo into as many different albums (like you can put a song into as many different playlists) without creating copies. It also will allow to use keywords like you want. Also, the latest version includes face recognition (which works surprisingly well for a first-gen feature), GPS sorting, and also is strong at editing the photos (most consumers I know say they barely use photoshop anymore).

Adobe Lightroom (Windows or Mac – $299) – Lightroom is a more professional software, but it’s Adobe’s answer to iPhoto and Apple’s more professional software, Aperture. Lightroom doesn’t have face recognition or GPS, but is a much more powerful editor as well as a organizational program.

I’ll openly admit I"m a Mac-only user, so there may be Windows-only options I’m not familiar with. But if you have a Mac, definitely get iPhoto.

I work for www.tillate.com, photographers get in at all hours of the morning and have to edit, sort and upload to the site 80-200 photos by the following afternoon. Most people here use picasa, mainly because it is free, but it does the job just fine. Personally I use Lightroom, it is more powerful, better for editing, but I only chose it because I had my box set up with adobe CS4 apps already.

If you’re really into photography I think Adobe Lightroom 2 is the way to go, fo sho. Maximum ability to edit photos and add tags and organize and search. It is definitely the best out there, although a little overkill if we are just talking snapshots. However I have used it to salvage several mistake snapshot photos. Its quite good with jpg’s and gives a lot of RAW options with jpg photos.

Thanks for all the advice. This is purely to be used as an organizational tool. 25 kids x 40 “categories” x ≥ 2 pics per category… 3x per year, is a lot of pictures to wade through…

I want to have time over the summer to play with it and see what will work bestest.

Frankly I don’t care what the photos look like – quality wise – so long as a boss type person can look at them and say “yes, this photo demonstrates that this child knows how to write the alphabet whilst standing on her head.” then I’m happy. Or, well, considerably less annoyed than usual.