The phrase “short-term pain, long-term gain” is one that crops up regularly when I discuss tagging photos as a way of handling large collections of images. Having just returned from a summer vacation with a few hundred photos to organize, I’ve undertaken trying to lessen the pain and increase the gain a bit. Thus far, I’m pretty happy with it. I imagine a year from now I’ll be thrilled to no end by it.

You’d be amazed at what tagging buys you. As a for instance, here’s a link to my photos on flickr that contain the tags jay and beach: Photos of Jay AND beach (note: you’ll need to be in my friends/family for that link to display a lot of photos).

The fact that i can do “and” searches as well as “or” searches on tags is incredibly powerful and lets me slice and dice my photo collection in a way where it is pretty easy for me to find whatever i’m looking for. Another example:
Photos tagged with Wilder and Beach and Jay will show me all of Jay’s beach pics that include members of my wife’s family.

WB contributors should think about tagging their photos when they post them on flickr, it will allow me to do some interesting scripting magic to pull in associated pictures on the fly. But on the whole, I advise anyone with a ton of images to start using tags on their photos. If the desktop software you’re using to manage your photos doesn’t support tags, then you should tag them once you upload them to flickr (and start looking for new software to manage your photos on your local machine). If you’re fortunate enough to be a Mac user, follow along the steps below, for herein is a first step towards easily organizing a few thousand photos (I’ve got 2702 in my collection as of today and the number is increasing exponentially).

How To use iPhoto with FlickrExport, Keyword Assistant and Flickr
What we’re aiming for here is:

• managing photos in iPhoto
• tagging photos in iPhoto
• uploading photos to flickr so that tagging done in iPhoto is carried over to flickr.

Managing photos in iPhoto
This is a no-brainer.

Step 1: Plug your camera in. If most of the pictures on your card are from the same event then give a roll name or description that makes sense for the bulk of the photos. If the photos are from a bunch of disparte situations then it’s probably not worth naming the roll. While you could give the pictures a date-related name, the date/time info is embedded in the photo data itself so you’d be storing redundant data.
Step 2: Prune and Rotate. After I dump the photos from card to iPhoto I do a quick round of editing to delete anything that’s clearly garbage and rotate any pictures that need to be rotated.
Step 3: Rename Titles. This is pretty much optional. If your card has pics from one event then you named the photos already. If not, I don’t really sweat the titles unless a particular picture is really screaming for a title.

Tagging photos in iPhoto
This is the “short-term pain” part of the process.

Tagging in iPhoto used to be a major pain in the ass for me and for my first two years or so of pictures, I hardly used tags because it was such a pain in the ass to assign them to photos. Then came Keyword Assistant. You can read more about Keyword Assistant in the README file. Basically, you install it and restart iPhoto and launch it via the new KA menu you have or via a hotkey sequence. KA does so much that it’s hard to really do it justice here, you just need to use it. A few points though:

• If you’ve got a screen full of shots and you want to assign just some of them the same tag or tags, you can option-click on the photos you want to assign the tag to, enter the tag in keyword assistant and hit enter.
• KA asks you to confirm before you use a keyword you’ve never used before. This is helpful when you can’t rememeber if you’ve been tagging all your kids photos with “kid” or “kids.”
• There is a hotkey sequence that allows you to move to the next photo once you tag the current photo. Learn it and use it. It makes it insanely easy to tag a card full of pictures in just a few minutes. (As a benchmark, I tagged about 700+ photos over a period of two nights while watching Dog the Bounty Hunter).

Uploading photos to Flickr
There are several options for uploading to flickr, but only FlickrExport is worth using.

First you need to get and install FlickrExport from Fraiser Speirs. You also (it should go without saying) need a flickr account.
Once you get the exporter installed, go to iPhoto and select the photos you’ve just tagged. Then go to the Share menu and click Export. You’ll see a new tab for Flickr on the export tool. Click it. The first time you use it you’ll need to authenticate your flickr account.
At this point, you’ve got your photos selected and (because FlickrExport is a great application) all of your tags are associated with the photos. The only remaining step is to decide whether or not you want to change the privacy settings for the photos. Fortunately, once you set it for one photo, you can just click “Apply to all” and all the photos will be private/public, etc.
It’s worth noting the FlickrExport isn’t a totally perfect application. Sometimes, especially when uploading a large number of files, it just chokes and doesn’t tell you why it failed. I think I’ve got it narrowed down to being an issue with .tif files. For most folks this shouldn’t be an issue but if your photos are .tif instead .jpg you may want to find a way to batch convert them before you upload to flickr.

Now you’ve got tagged photos on flickr. When you’re viewing your flickr homepage, you’ll see a link for your tags. Click it. From there you can search through multiple tags.

UPDATE: If you haven’t already done so, you should probably read Getting The Most Out of Flickr