Ok, so, I'm about 5 years behind the curve, even though I'm a supposed professional Web 2.0 developer, but I'm just now getting into Flickr. Also, I really like taking screenshots of interesting things using CMD+SHIFT+4 and uploading those to a "Screenshots" Flickr photoset. Here's what I wanted to do to to feed my Screenshots Flickr set: Take a screenshot and have it automatically imported into iPhoto, and then upload it from iPhoto to Flickr. Will it "Just Work?" No, it does not. See my rant here.

Save Screenshots in a Special Folder

Download Deeper. Deeper is a Mac app that let's you tweak many hidden settings for your Mac. The only one I use is customizing the name of screenshot images and the location to which they are saved. I save my screenshots in [me]/Pictures/screens/ and each one is prefixed screen.

Automatically Import into iPhoto

iPhoto cannot "watch" a folder and automatically import images dropped into it. Instead, and disappointingly, you must become a pseudo-programmer and create an Automator workflow to perform this action for you. Automator is a program that lets you create workflows to, well, automate repetitive tasks, such as importing images into iPhoto. Here's what you do:

1. Download Deeper, mentioned above, and configure it to save your screenshots to a Folder. I chose Pictures/Screens
2. Open iPhoto and create an album to hold your screenshots. I called it Screens, too.
3. fire up Automator, which lives in Application/Automator and create a new Custom workflow.
4. Add "Get Specified Finder Items" to the list and use the Add... button to add the folder where your screenshots will land when created
5. Add "Import Files into iPhoto" and choose Existing album and Screens
6. Save it as a Folder Action: File - Save As Plug-in... and give it a name.
7. Choose Plug-in for: Folder Actions and Attached to Folder: screens or wherever your folder new screenshot folder resides.

Now, take a screenshot and see if iPhoto fires up and imports the image. If so, great! If not... well, maybe I messed up, maybe you did. I'm that helpful.