You can find a copy of my PowerPoint slides, paper, and even a video with my narration of the slides at: http://www.thinkgenealogy.com/2008/04/06/10-things-genealogy-software-should-do/
It may be more genealogist focused but I am always interested in hearing about what tools you are using, what is making you frustrated, and how things might be simplfied.
You can add these comments to: http://www.thinkgenealogy.com/2008/01/08/what-do-you-wish-genealogy-software-did/
I think today’s genealogy software is good, but that it can be even better. There are many scenarios (similar to yours) that are not currently being addressed. The field is ripe for more software developers and designers to take those scenarios and make a living solving those problems. I’m optimistic that will happen.