I think it would be very valuable to try and do a big compare-and-contrast analysis of the Python 2->3 transition vs the ruby 1.8->1.9(->2) transition.
ruby 1.9 transition was actually a pretty big pain (I have no idea whether as big a pain as python2->3 or not, that'd be something to look at).
But the ruby ecosystem/community has successfully moved to 1.9, there is little left on 1.8.
On the other hand, sometimes it's _really_ frustrating how much work I need to spend upgrading my ruby stuff to use the latest and greatest. Ruby community is relatively uncaring about backwards compat (less than python? I am not sure. Is that uncaringness part of the tradeoff that got us to all move to ruby 1.9 somehow? I don't know, but that's what I'm wondering. Many interesting questions.)
PHP4->PHP5 was a big breaking change as well. It took several years for all projects nad hosting companies to upgrade and switch to v5 by default.
But there was a strong push from developers. I don't see that happening when Python developers' attitude is "Meh, Python 2 is all right, I don't need to upgrade anything ever".
Python 2 is nowhere near as lacking as PHP4. Which is probably a big part. But even then it took a big campaign and large software like Wordpress declaring that they would go PHP5 only.
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I think it would be very valuable to try and do a big compare-and-contrast analysis of the Python 2->3 transition vs the ruby 1.8->1.9(->2) transition.
ruby 1.9 transition was actually a pretty big pain (I have no idea whether as big a pain as python2->3 or not, that'd be something to look at).
But the ruby ecosystem/community has successfully moved to 1.9, there is little left on 1.8.
On the other hand, sometimes it's _really_ frustrating how much work I need to spend upgrading my ruby stuff to use the latest and greatest. Ruby community is relatively uncaring about backwards compat (less than python? I am not sure. Is that uncaringness part of the tradeoff that got us to all move to ruby 1.9 somehow? I don't know, but that's what I'm wondering. Many interesting questions.)
PHP4->PHP5 was a big breaking change as well. It took several years for all projects nad hosting companies to upgrade and switch to v5 by default.
But there was a strong push from developers. I don't see that happening when Python developers' attitude is "Meh, Python 2 is all right, I don't need to upgrade anything ever".
Python 2 is nowhere near as lacking as PHP4. Which is probably a big part. But even then it took a big campaign and large software like Wordpress declaring that they would go PHP5 only.
Lots of apps die in the wake of the new.