The Java 8->11 transition was rough but honestly after that we've not really experienced a whole lot of pain. 16 has been a little bit of a pain as well since it closed some more unsafe holes. I think that's the last release, however, that's going to cause major headaches with migrations.
I'm speculating though.
Java has been slowly adding the best kotlin features (such as data classes, records) which also makes it a bit harder to sell.
That said, I've introduced kotlin on a few teams and pretty much everyone that's worked with it has complimented it.