I have the (perhaps uncommon) issue of running WordPress on the same server that I store all of my images. This makes it a bit annoying to upload images to my blog, since it requires I manually download all of them, resize them and then re-upload. This normally just results in me giving up and not posting pictures, which is a shame, because I’m sure you’re all very interested in the mundane details of my life.
Anyhoo… I found a solution for my problems in a combination of 2 plugins – Add From Server, and Imsanity. Add From Server allows me to simply select a directory of files on my server and have them bulk imported. On it’s own, this wouldn’t be enough, because then I would end up with a whole bunch of 10M images files that no one would be interested in looking at. Imsanity magically hooks into the import process and enforces some sizing guidelines – in this case limiting the WordPress images to 1600×1200.
Yay for pluggability!