So in reference to Adam's comment, can we do something better for the user? Best usability surely implies that as per my original 3rd point, that questions of the user should occur at the beginning or end of the upgrade. I don't believe repeated interruptions during the upgrade give a good feeling. Ideally all questions can be asked at the beginning, that way a user is going to be sure he has gathered all the information prior to committing to an upgrade. Sure, this might mean a rearchitecture of the debian-installer or dpkg even, but I think it should be investigated. The main reason I never got into Debian a few years ago was the fact that the install process took so long as you never were quite sure you weren't going to be asked more questions. Certainly for fresh installs Ubuntu has this sorted, but my concern is during an upgrade, people often allocate time to do this, walk away at the beginning of installation and hope to come back in 30 minutes and find it done. The current architecture does not seem to allow this.
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