The good thing is that Scala is a typed language, so they can
a) provide tooling for migrating code
b) compile things and get clear information about how much differences there are
I think somebody said that necessary lines of change from Scala 2 -> Scala 3 should be below 0.1% to be acceptable.
But Python changed Strings to use Unicode, and that's something everybody uses and that is insanely hard to refactor automatically even with types.
For Dotty, instead, there are some hard-to-refactor-for changes, but they're in really advanced Scala things, so I expect they'll affect fewer users — mostly the kind of users who can write shapeless-like stuff.
Also xml support as the scala-xml library will continue. Though as the xml literals are removed you have to use string interpolation (xml"<your><xml/>here</your>") which isn't as nice to use. (hopefully someone comes up with a nice DSL or something instead)