I've just got a review copy of The Long Tail. I've been following the blog for a while so I thought I'd share some relevant thoughts as it applies to charities before I dive into the book.
The Long Tail premise is, in the subtitle of the book "Why the Future of Business Is Selling Less of More". A non-profit IT director writes on the subject, but I'll speculate further.
Small charities need to make themselves findable. Guidestar in the UK is a start (also available in the US). A Dutch student is working on Helpalot.org, "a website that makes every charity findable". That's a one person effort though.
If I were in a small charity rather than the medium one I'm in now, I'd be wondering how I could create a web presence without too much work (I'm not aware of some easy options), how I could take donations (CAF looks simple, but we've struggled with the paperwork they send you to tell you about the gifts), and how I could get found on the Internet.
So far there's no iTunes for charity, unless you know about it...