Restisting the temptation to rely on Ubuntu for Django 1.11
One of the things that is on my mind is what to do about our Django web application as far as Python 3 goes. Right now it's Python 2, and even apart from people trying to get rid of Python 2 in general, the Django people have been quite explicit that Django 1.11 is the last version that will support Python 2 and that support for it will end in 2020 (probably 'at the start of 2020' in practice). Converting it to Python 3 is getting more and more urgent, but at the same time this is going to be a bunch of grinding work (I still haven't added any tests to it, for example).
The host that our Django web app runs on was recently upgraded to Ubuntu 18.04 LTS, so the other day I idly checked the version of Django that 18.04 packages; this turns out to be Django 1.11 (for both Python 2 and Python 3; Django 2.0 for Python 3 might just have missed Ubuntu's cutoff point, since it was only released at the end of 2017). Ubuntu 18.04 LTS will be supported for five years and Ubuntu never does the sort of major version updates that going from 1.11 to 2.x would be, so for a brief moment I had the great temptation to switch over to the Ubuntu 18.04 packaged version of Django 1.11 and then forgetting about the problem until 2022 or so.
Then I came to my senses, because Ubuntu barely fixes bugs and security issues at the best of times. To my surprise, Ubuntu actually has Django in their 'main' repo, which is theoretically fully supported, but in practice I don't really believe that Canonical will really be spending very much effort to keep Django 1.11 secure after the upstream Django developers drop support for it. No later than 2020, the Ubuntu 18.04 LTS version of Django 1.11 is very likely to become, effectively, abandonware. Unless we feel very confident that Django 1.11 will be completely secure at that point in our configuration, we should not keep running it (especially since a small portion of the application is exposed to the Internet).
(I wouldn't be surprised if Canonical backported at least some easy security fixes from 2.x to 1.11 after 2020. But I would be surprised to see them do any significant programming work for code that's significantly different between 1.11 and the current 2.x or for 1.11-specific issues.)
However much I'd like to ignore the issue for as long as possible or let myself believe that it can be someone else's issue, dealing with this is in my relatively immediate future. We just have to move our Django web app to Python 3 and Django 2.x, even though it's going to be at least a bit of a grind. Probably I should try to do it bit by bit, for example by spending even just an hour or a half hour a week adding a test or two to the current code.
(Part of why I feel so un-motivated is that we're going to have to invest a bunch of effort to wind up exactly where we are currently. The app works perfectly well as it is and we don't want anything that's in newer Django versions; we're upgrading purely to stay within the version coverage of security fixes. This is, sadly, a bunch of make-work.)