IANAL but, at least as a practical matter, anything along these lines that's done for personal/internal use seems likely fair game. Someone is seriously going to make a case that I can't transcribe a copy of a speech or other recording for my own use?

It's external distribution that gets stickier--especially as you get beyond short excerpts to a full and complete work.

ADDED: And, yes, anyone can sue anyone for anything. But arguments that something could technically be construed as a legal violation even though no one has ever been called on it in the history of the legal system aren't terribly convincing.