Case 1
Given that myListener "is not used anywhere else" and therefore I assume, a [method-] local variable, the answer is no. In the general case though, the answer is mostly a no but can sometimes be a yes.
As long as myListener is strongly reachable, then it will never become eligible for finalization and it will continue to consume memory. For example, this would be the case if myListener is a "normally" declared static variable (all "normal" references in Java are strong references). However, if myListener is a local variable, then the object will not be reachable anymore after the return of the current method call and bool.removeListener(myListener) is a bit meaningless over-engineering. Both the observer and the Observable goes out of scope and will eventually be finalized. A quote from my own blog post about this answer might paint a better picture:
It doesn’t matter if the box know about the cat inside of it, if you
throw the box into the ocean. If the box isn't reachable, nor is the
cat.
Theory
To fully understand the situation here, we have to remind ourselves of the life-cycle of a Java object (source):
An object is strongly reachable if it can be reached by some thread
without traversing any reference objects. A newly-created object is
strongly reachable by the thread that created it. [..] An object is
weakly reachable if it is [not] strongly [..] reachable but can be
reached by traversing a weak reference. When the weak references to a
weakly-reachable object are cleared, the object becomes eligible for
finalization.
In the case of static variables, these will always be accessible as long as the class is loaded, thus reachable. If we didn't want a static reference to be the one that hinder the garbage collector to do his job, then we could declare the variable to use a WeakReference instead. JavaDoc says:
Weak reference objects [..] do not prevent their referents from being
made finalizable, finalized, and then reclaimed. [..] Suppose that the
garbage collector determines at a certain point in time that an object
is weakly reachable. At that time it will atomically clear all weak
references to that object [..]. At the same time it will declare all
of the formerly weakly-reachable objects to be finalizable.
Explicit management
For illustration, let's assume that we write a JavaFX space simulation game. Whenever an Observable planet moves into the view of a spaceship observer, the game engine register the spaceship with the planet. It is quite apparent that whenever the planet goes out of view, the game engine should also remove the spaceship as an observer of the planet by using Observable.removeListener(). Otherwise, as the spaceship continues to fly through space, memory will leak. Eventually, the game cannot handle five billion observed planets and it will crash with an OutOfMemoryError.
Do note that for the vast majority of JavaFX listeners and event handlers, their life-cycle is parallel to that of their Observable so the application developer has nothing to worry about. For example, we might construct a TextField and register with the text field's textProperty a listener that validate user input. As long as the text field sticks around, we want the listener to stick around. Sooner or later, the text field is not used anymore and when he is garbage collected, the validation listener is also garbage collected.
Automatic management
To continue on the space simulation example, assume that our game has limited multiplayer support and all the players need to observe each other. Perhaps each player keep a local score board of kill metrics or perhaps they need to observe broadcasted chat messages. The reason is not the important point here. What would happen when a player quit the game? Clearly, if the listeners are not explicitly managed (removed), then the player who quit will not become eligible for finalization. The other player's will keep a strong reference to the offline player. Explicit removal of the listeners would still be a valid option and probably the most preferred choice for our game, but let's say that it feels a bit obtrusive and we want to find a more slick solution.
We know that the game engine keep strong references to all players online, for as long as they are online. So we want the spaceships to listen for changes or events of each other only for as long as the game engine keep the strong references. If you read the "theory" section, then surely a WeakReference sounds like a solution.
However, just wrapping something in a WeakReference is not the entire solution. It seldom is. It is true that when the last strong reference to the "referent" is set to null or otherwise become unreachable, the referent will be eligible for garbage collection (assuming that the referent cannot be reached using a SoftReference). But the WeakReference is still hanging around. The application developer need to add some plumbing so that the WeakReference itself is removed from the data structure he was put in. If not, then we might have reduced the severity of the memory leak but a memory leak will still be present because dynamically added weak references consume memory too.
Lucky for us, JavaFX added interface WeakListener and class WeakEventHandler as a mechanism for "automatic removal". The constructors of all related classes accept the real listener/handler as provided by client code, but they store the listener/handler using a weak reference.
If you look at the JavaDoc of WeakEventHandler, you'll notice that the class implement EventHandler, so the WeakEventHandler can be used wherever an EventHandler is expected. Likewise, a known implementation of a WeakListener can be used wherever an InvalidationListener or a ChangeListener is expected.
If you look into the source code of WeakEventHandler, you'll notice that the class is basically only a wrapper. When his referent (the real event handler) is garbage collected, the WeakEventHandler "stop working" by not doing anything at all when WeakEventHandler.handle() is called. The WeakEventHandler doesn't know about which object he has been hooked up with, and even if he did, the removal of an event handler is not homogeneous. All known implementing classes of WeakListener has a competitive advantage though. When their callbacks are invoked, they are implicitly or explicitly provided a reference to the Observable they are registered with. So when the referent of a WeakListener is garbage collected, eventually the WeakListener implementation will make sure that the WeakListener itself is removed from the Observable.
If it is isn't already clear, the solution for our space simulation game would be to let the game engine use strong references to all online spaceships. When a spaceship goes online, all other online spaceships are registered with the new player using a weak listener such as WeakInvalidationListener. When a player goes offline, the game engine remove his strong reference to the player and the player will become eligible for garbage collection. The game engine doesn't have to bother about explicit removal of the offline player as a listener of the other players.
Case 2
No. To better understand what I'll say next, please read my case 1 answer first.
BooleanPropertyBase store a strong reference to otherBool. This in itself does not cause otherBool to always be reachable and thus potentially cause a memory leak. When bool becomes unreachable, then so do all its stored references (assuming they are not stored anywhere else).
BooleanPropertyBase also works by adding itself as an Observer of the property you bind it to. However, it does so by wrapping itself in a class that works almost exactly like the WeakListeners described in my case 1 answer. So once you nullify bool, it will be only a matter of time before it is removed from otherBool.
