I have been following a number of stories like this,Congress Follows Email Trail - WSJ.com, about the Whitehouse use of RNC controlled email accounts to discuss the firings of federal prosecutors. The law appears quite clear. Official Whitehouse email is a document that must be retained. Discussions of firing federal prosecutors sounds official to me. Therefore the Whitehouse was wrong to use outside email addresses to keep the discussions secret. I am not comfortable with the law in the first place. Email and other electronic communication media like chat and IM are often used more like casual conversation than formal memos. Few would argue that the President's every word should be recorded at all times. It would make discussion and debate next to impossible. In the process of thinking through an issue one may consider many potentially unpopular ideas, if only for the purpose of argument. Free and unconstrained give and take generally leads to be best understanding and decisions. Free and unconstrained debate can not take place with the world looking over your shoulder and scrutinizing every word.
If we accept that email and chat are used like conversation to hash out ideas, then it is very damaging to the process to place heavy recording and monitoring requirements on it. At the same time, having no oversight substantially reduces accountability. It might even facilitate corruption.
This really shows in a microcosm the greater question of general communications privacy vs. law enforcement access. It is a hard balancing act because there is very little middle ground. Basically you are either monitored or not. Having monitoring of a random half of the messages is going to make everyone unhappy.