So after reporting my Bluetooth woes yesterday, I decided that I may as well bite the bullet and write a full application to do the job. Phone2Flickr is a .NET application which will sit in your system tray and upload your phone photos to Flickr when it comes in range. This has gone under only limited testing with two Samsung phones so I'm not sure how it will handle others, plus I've only used it on my PC. This is seriously an alpha release.
You have to pair your phone with your PC in the normal way, using the Control Panel Bluetooth applet, and you also need to make the PC an authorised device on your phone otherwise you'll have to keep allowing the PC to perform actions. How you do this will vary on your phone model.
This software currently requires .NET Framework 3.5, and that your phone supports the Obex File Transfer service. The UI for this stinks. Chances are it won't work for your device. But I wanted to get something online as it will give me impetus to improve it. I'm also releasing the source code, and will most likely accept patches.
Phone2Flickr 0.1 is something I built for my own use which I hope others will enjoy. Please don't expect too much!