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.)