The Association of Research Libraries has released a pre-publication version of "Copyright Risk Management: Principles and Strategies for Large-Scale Digitization Projects in Special Collections."
Here's an excerpt:
Copyright law often seems unmanageably complex, leading librarians to focus too much on a single aspect of a project and, when that aspect proves inapplicable, to give up the proposed digitization. But the multifaceted nature of the law, especially its variety of limitations and exceptions, should really be seen as an invitation to a holistic evaluation that focuses on risk and considers how each facet can contribute to a risk reduction strategy. If this is done consistently as digitization projects are undertaken, the risk of infringement litigation will usually be seen to be much more manageable, and a great deal of unnecessary self-censorship will be avoided.
See also the pre-publication version of "Digitization of Special Collections and Archives: Legal and Contractual Issues."