And fifth, there's the possibility that your boss is also under a requirement to provide a status report

Indeed. Having a good status reporting system and a solid paper trail can save an enormous amount of legal hassles when it comes to contract disputes. You often find that requests for these sort of papertrails start in a legal department (or after a costly dispute ;-)

I found the best way to do them was to waste a lot of time writing a bunch of perl scripts to help me keep my timesheets and produce appropriate summary reports ;)