I've been spending a fair amount of time considering the free vs paid content debate, and have come to the conclusion that they have completely different roles in an online publishing strategy.  The paid content needs to be targeted at your core, and be demonstrably valuable.  The free content needs to be targeted at the new entrants in your market who could at some point move into your core group, and needs to be designed to be visible on search and capture the imagination.  So rather than just sort your current content into a free pile and a paid pile, you may need to repackage both, and maybe even have different people creating each.  The last step is to have a clear path from the free stuff to the paid stuff.  I've expanded on these ideas in my recent blog at: http://www.penmaen-media.co.uk/index.php/2009/10/why-content-is-marketing/. I'd be interested in the experiences and views of other publishers.  Carolyn