I have really bad memories of the change between puppet 2 and 3 for example.
The puppet migration was definitely more painful, because of the entangled code.
There are inherent problems in the TF framework and the migraitons. 0.12 introduced for loops, and 0.13 added modules support to them. So a proper migration should convert deduplicate resources into lists of resources. This is painful for big models, since one needs to write scripts in order to convert resource associations in the statefile. And hope not to miss anything!
Due to the strictly declarative nature, it's also difficult to slowly move duplicated resources into lists, and handle both of them at the same time.
At this time, our time is stuck with a certain TF version, and can't move without spending considerable resources.