I've decided I'll port DWiki to Python 3, but not any time soon
At this point I have only one significant Python 2 program that I care deeply about and that is DWiki, the pile of code that underlies Wandering Thoughts. What to do about DWiki in light of Python 3 has been something that has been worrying and annoying me for some time, because doing a real port (as opposed to a quick bring-up experiment) is going to involve a lot of wrestling with old code and Unicode conversion issues. Recently I've come around to a conclusion about what I plan to do about the whole issue (perhaps an obvious one).
In the end neither grimly staying on Python 2 forever or rewriting DWiki in something else (eg in Go) are viable plans, which leaves me with the default: sooner or later I'll port DWiki to Python 3. However I don't expect to do this any time soon, for two reasons. The first is that Python 3 itself is still being developed and in fact the Python landscape as a whole is actively evolving. As a result I'd rather defer a port until things have quieted down and gotten clearer in a few years (who knows, perhaps I'll want to explicitly revise DWiki to be PyPy-friendly by then). As far as I'm concerned the time to port to Python 3 is when it's gotten boring, because then I can port once and not worry about spending the next few years keeping up with exciting improvements that I'd like to revise my code to take advantage of.
The second reason is more pragmatic but is related to the rapid rate of change in Python 3, and it is that the systems I want to run DWiki on are inevitably going to be behind the times on Python 3 versions. Right now, the rapid rate of improvements in Python 3 means that being behind the times leaves you actively missing out on desirable things. In a few years hopefully that will be less so and a Python 3 version that was frozen a year or three ago will not be so much less attractive than a current version. This too is part of Python 3 slowing down and becoming boring.
(If you are saying 'who freezes Python 3 versions at something a few years old?', you haven't looked at long term support Linux distributions or considered how long people will run eg older FreeBSD versions. There is a long and slow pipeline from the latest Python 3 release to when it appears in OS distributions that many people are using, as I've covered before.)
I don't have any particular timeline on DWiki's Python 3 port except that I don't intend or expect to do this within, oh, the next three years. Probably I'll start looking at this seriously about the time the Python developers start clearing their throats and trying to once again persuade everyone that 2.7 support will be dropped soon, this time for sure. A clear slowdown in Python 3 development plus OS distros catching up to current versions might push that to sooner, but probably not much sooner.
Hopefully thinking through all of this and writing it down means that I can stop worrying about DWiki's future every so often. I may not be doing anything about it, but at least I now have a reasonable plan (and I've kind of made my peace with the idea of going through all the effort to get a production quality version of DWiki running under Python 3 (and yes, the amount of effort it's going to take still irritates me and probably always will)).
(Although every so often I toy with the idea of a from-scratch rewrite of DWiki in Go that addresses various things I'd do differently this time around, the reality is that DWiki's creation took place in unusual circumstances that I'm unlikely to repeat any time soon.)