I could reproduce all this behavior here.
The main reason for this is (imho!) because of a little (maybe forgotten?) bug 
in the update-rc.d script:
Quote 'man update-rc.d':
"..Obviously, therefore, the default stop sequence number should be 80.  
Defaulting to 20, as update-rc.d does, is an old bug .."
It defaults setting the simlinks to 20. As a result, the sendsigs init-script 
tries to kill all remaining processes while some network filesystems (nfs, 
cifs, smb) are not yet umounted and/or the networking is not yet stoped etc..
Those symlinks (/etc/rc0.d/S20sendsigs and /etc/rc6.d/S20sendsigs) must be 
simply renamed to put them on '80', resulting in /etc/rc0.d/S80sendsigs and 
/etc/rc6.d/S80sendsigs.

This should fix this (it did for me reproducable):
Copy&Paste this Code in your terminal (all in one line):

  sudo update-rc.d -f sendsigs remove && sudo update-rc.d sendsigs
start 80 0 6 .

(The last . (dot) is part of the code!)

h.t.h.
Raphael Gradenwitz

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Jaunty & Interpid: won't power off on shutdown or reboot
https://bugs.launchpad.net/bugs/326988
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