The last time, I was apprehensive about upgrading. In the past when I've done it, there were several things I didn't like happen.
1. Old settings were carried over literally. There was no way to use the new settings if you use the previous home directories. This happened during an upgrade. I am quit surprised that the newer version of the software, especially for something as important as GNOME, did not notice that the config file was from a previous version and at least offered to replace it with a new version. I understand the concern to keep all the user's settings but should there be an updater program for that.
2. Certain software that were there previously, were not replaced but simply disappeared. This happens especially for software that is not in the vogue or part of the core distribution. I understand that leaving the program there is risking a certain incompatibility but at least if it was there before and there is no replacement during the upgrade, please offer me to leave it there. It happened to Nagios, a network monitoring software I use. It just disappeared. I had to reinstall and reconfigure it every time I upgraded. It is only on the contrib section.
An upgrade is an upgrade, not re-installation and certainly not a fresh installation. Distribution packagers should respect that or loose their user base.
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