There is a real problem here in that we really need to update to newer packages – a lot in Jessie are very old indeed, and since we follow the Debian distribution, we get what they (after months of testing) use.

I’m surprised some packages are now older version -that seems very odd. A list would be useful, as would a list of popular packages that are no longer present. Again this is actually down to Debian from which we get the packages lists, then add some Pi specific stuff.

As for third party stuff no longer working, it’s impossible for us to test everything that might ever be run on a Pi to ensure it still works. We have to leave that down to the maintainers of whatever package it is. So for example, PiFace will need to update their libraries to work with Stretch. They are clearly the best people to do this since they know the code. This process usually takes a few weeks after a major upgrade like this, time for third party suppliers to fix code and update their libraries. Same happens with Windows releases as well.

Documentation is indeed an issue. However, if we delayed OS releases so we can update all the docs, they would be delayed by months, possible years, due to lack of staff to get that documentation updated. It’s possible for us to update after the event over a longer period of time, but does mean the docs lag behind. I’m not sure what can be done about that apart from throwing $1M at the problem and employing a load of people just to keep docs updated. Unfortunately, that’s a lot of cash, that people would argue is better spent elsewhere.