In answer to your first question, it should be as simple as replacing:
when(LoggerFactory.getLogger(GoodbyeController.class)).thenReturn(loggerMock);
with
when(LoggerFactory.getLogger(any(Class.class))).thenReturn(loggerMock);
Regarding your second question (and possibly the puzzling behavior with the first), I think the problem is that logger is static. So,
private static Logger logger = LoggerFactory.getLogger(GoodbyeController.class);
is executed when the class is initialized, not the when the object is instantiated. Sometimes this can be at about the same time, so you'll be OK, but it's hard to guarantee that. So you set up LoggerFactory.getLogger to return your mock, but the logger variable may have already been set with a real Logger object by the time your mocks are set up.
You may be able to set the logger explicitly using something like ReflectionTestUtils (I don't know if that works with static fields) or change it from a static field to an instance field. Either way, you don't need to mock LoggerFactory.getLogger because you'll be directly injecting the mock Logger instance.