Flickr Upload is great it lets you drop files on it and then uploads them to Flickr. It’s a pain if the files are already sorted and arranged, because all this is lost. All the files at all the levels go in one group.
I went looking for something that would treat each folder as a tag and the lowest folder would be the set. I couldn’t find something, but I did find enough info to make something to do this. Explorer Sync started today and it already scans through the folders and upload the files as I described above. It’s still very crude. Right now there is one button and everything is hard coded. I downloaded MS Visual Studio Express 2005, SP1, FlickrNet, and NUnit. Using this thin document I got the Flickr part working. And this article shows how to iterate the folders. The interface needs to let you pick a root folder and some tweaks to the uploading and tagging. At this level it solves my immediate problem, v.1. I want to keep from uploading files twice. Maybe, by storing the filepath in the comments on Flickr.
For extra credit, I want to let multiple people make comments or tag the photos on Flickr and carry this info back to the Windows file metadata. Then I can see what comments people make and move/update the photos accordingly. Oddly, there is not a .Net NTFS metadata API. You have to make an Interop to the old Win32 libraries. I found someone who did this with c#, but is is not working on my Vista.
Took about 5 hours so far. I would guess it’s about 33% done or less. The rest will probably take 15-20 more.