How about doing the following now (Lazy Web and Andy and whoever wants to participate):
Write a Python or Java app that does the following
1. Prompts for a title
2. For each image in the default camera image folder, it uploads them to Flickr using their photo upload API

Pretty simple and pretty dumb but I've learned that if you can't do the simple stuff, you are "stuffed". So if anybody wants to code this for me :-) or post some code that does this, I would be grateful and I will take it from there (and post updates here).