With regards to point number 1:

1. First of all, if the updater crashes with a stack trace, a dialog should 
appear to report the error.
    Pointing to the log file, which I later found out to be 
/var/log/dist-upgrade/main.log, would be helpful.
   I waited several minutes, thinking that it was busy in the background.

I would expect the upgrader to present you with a crash dialog and a bug
reporting wizard to be launched.  Do you have a crash file in
/var/crash?  It would be named after the binary so something like
_usr_bin_update-manager.

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https://bugs.launchpad.net/bugs/1254447

Title:
  Upgrade to 13.30 crashes because of hidden file

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