For some applications (though not necessarily all), it might help if the OTRS process was replaced by a standard online permission form rather than having Wikimedians negotiate with outsiders in the hope of getting them to say magic words.
I might imagine a process somewhat like the following:
1) User identifies some materials they would like to use on Wikipedia. 2) They upload copies to some "staging area". 3) They use a utility to prepare a standardized permission form for the item(s) in question. 4) Through Wikimedia they send an email to the copyright holder explaining the situation, and asking them to visit the online form to give their permission 5) Once approved, the materials could be automatically moved to Commons, etc.
Presumably such a form would provide a standard explanation of what's going on and selection of acceptable Wikimedia licenses. Hopefully such a thing would remove the problem with statements being unclear or legally insufficient.
Obviously such a process could be embellished with additional contacts between the Wikimedians and copyright holders, etc., but the above could serve as a baseline.
Anyway, that's my idea. I realize that in some ways it runs counter to Milos's complaint, since it requires a new process rather than cutting out bureaucracy per se. However, I think having a fixed and standardized approach for free content releases would ultimately cut down on arguments.
-Robert Rohde