After seeing HoudaGeo in actiona few weeks ago, i came as close as i ever have to breaking down and buying a mac to manage my media.  Then on a Snowy day in Valdez, I found what could be the easiest, coolest piece of software to bridge the gap between web interfaces, portable devices, and life experience.   

 www.robogeo.com - Image Geotagger for Windows

Not only does it tag your photos, but it exports directly to flickr (as seen here), To a google map, google earth, or just a directory with the geodata in your EXIF file.  i'll be posting all of my images at www.flickr.com/frumkinwy, and likely turning my clients on to it as quickly as possible.