Examining Paid Online Content Models

Paid content online is getting renewed scrutiny in the press these days, especially now that publishers are leaving no stone unturned while looking for new sources of revenue. As audience developers, circulators and otherwise specialists in the art of conversion,what are the immediate red flags, opportunities or suggestions you'd have if you were sitting in a corporate strategy meeting brainstorming the launch of a paid online content model? What are the customer-facing issues?