Gradle rot really is a pain, at least for Android projects (haven't used it in e.g. serverside stuff).
Proguard is fun too, with how it'll carve out or break chunks of functional code if you don't spell out precisely what shouldn't get deleted/obfuscated.
Gradle is pretty sane, from my backend dev experience. But you indeed can get in a situation when dependencies become slightly incompatible after an attempt to upgrade, and you have to fix your code or juggle version requirements, much like with npm or pip.
Proguard is fun too, with how it'll carve out or break chunks of functional code if you don't spell out precisely what shouldn't get deleted/obfuscated.