Hello!
My problems have all been with in-place upgrades on the six-month major releases - all the more reason to run LTS versions
Valtam, you're right on target with that one. There are many thousands of different programs in the repositories, developed by thousands of different programmers. No one group could ever check them all every time they're updated. More or less, that responsibility is left to the program's developer.
Actually, in the Ubuntu repositories, the opposite problem is true - the latest versions there are often several versions behind the current ones. VLC media player is a good example of what I'm talking about. The down side to that is that the programs that are broken take that much longer to get fixes down the pipeline. Sometimes current versions can be downloaded elsewhere as a .deb, but more often than not, if you want everything to be bleeding-edge, you must compile them yourself from source or fool with tarballs (.tar files).
Lauchpad.net is a good place to find out about the latest goings-on with packages you're interested in - especially bugs, and their progress towards getting them fixed. Synaptic lets you tweak what kind of stuff is updated and how often, or not at all. Perhaps one day, Synaptic might be able to accommodate setting up an update strategy for each individual file, but if you have a lot of files, the necessary database could get big (and slow).
For the REALLY paranoid, one can always back up before updating...
73 DE N4RPS
Rob