IPv6 and Python3 are case studies in how not to roll out a new version unless you're cool with multi-decade upgrade windows.
It took ages, but there was at least a "best effort" to help people write code that could be easily moved between 2 and 3. (In spite of apparent behavior from the Python developers at the time).
IPv6's hard break with IPv4 means that the switchover likely won't happen anytime soon.